CN103328438A - Aryloxyurea compound and pest control agent - Google Patents

Aryloxyurea compound and pest control agent Download PDF

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Publication number
CN103328438A
CN103328438A CN2011800488895A CN201180048889A CN103328438A CN 103328438 A CN103328438 A CN 103328438A CN 2011800488895 A CN2011800488895 A CN 2011800488895A CN 201180048889 A CN201180048889 A CN 201180048889A CN 103328438 A CN103328438 A CN 103328438A
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China
Prior art keywords
substituent
replacing
replace
alkyl
compound
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CN2011800488895A
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Chinese (zh)
Inventor
古川裕纪
中村武彦
玉伊彻生
花井大辅
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Nippon Soda Co Ltd
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Nippon Soda Co Ltd
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Priority to CN201610213506.XA priority Critical patent/CN105859590B/en
Publication of CN103328438A publication Critical patent/CN103328438A/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
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    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
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    • A—HUMAN NECESSITIES
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    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
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    • A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
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Abstract

The present invention provides a pest control agent, an acaricide, or a bactericide that contains, as the active ingredient thereof, at least one type of compound selected from aryloxyurea compounds represented by formula (V) (wherein R1 to R5 each independently represent an alkyl group or the like, X is a halogen atom or the like, n is an integer of 0 to 5, and Z is an oxygen atom or a sulfur atom) or salts thereof.

Description

Aryloxy carbamide compound and noxious organism control agent
Technical field
The present invention relates to novel noxious organism control agent.More specifically, the present invention relates to have the industrial favourable synthetic aryloxy carbamide compound of excellent acaricidal activity and/or fungicidal activity, characteristic and excellent in safety and energy and miticide and/or the sterilant take it as effective constituent.
The application is incorporated herein its content based on the Japanese Patent Application 2010-229617 number opinion right of priority of on October 12nd, 2010 in Japanese publication.
Background technology
As with compound of the present invention relevant compound structurally, the compound of formula (A)～formula (E) expression is disclosed in the patent documentation 1～5.
Figure GDA00003484046400011
In the above-mentioned formula, R 1Expression C1～6 alkyl etc.
R 2Expression hydrogen atom etc.
Figure GDA00003484046400012
In the above-mentioned formula, X 1Expression hydrogen atom, chlorine atom etc.
Y 1Expression hydrogen atom, chlorine atom etc.
R 3Expression phenyl etc.
R 4Expression hydrogen atom, low alkyl group etc.
R 5Expression hydrogen atom etc.
A represents carbon atom or nitrogen-atoms.
Figure GDA00003484046400021
In the above-mentioned formula, X 2Expression hydrogen atom, halogen atom, C1～8 alkyl etc.
Y 2Expression hydrogen atom, halogen atom, C1～8 alkyl etc.
R 6Expression phenyl, cyano group, C1～4 alkyl etc.
R 7Expression hydrogen atom, C1～4 alkyl etc.
R 8And R 9Represent independently hydrogen atom, C1～3 alkyl etc.
R 10Expression halogen atom, C1～4 alkyl.
Figure GDA00003484046400022
In the above-mentioned formula, X 3Expression chlorine atom, bromine atoms or methyl.
Y 3Expression chlorine atom, bromine atoms or methyl.
R 11Expression ethyl, n-propyl.
R 12The expression ethyl.
Figure GDA00003484046400023
In the above-mentioned formula, X 4And Y 4In a side represent nitrogen-atoms or oxynitride, the opposing party represents that CR(R represents hydrogen atom, halogen atom etc.), perhaps X 4And Y 4The two represents nitrogen-atoms.
Z 1Expression hydrogen atom, halogen atom etc.
R 13Expression alkyl, alkenyl etc.
R 14The benzyloxymethyl that the benzyl ring of expression benzyl moiety is at random got by C1～4 alkoxyl groups replacement etc.
R 15And R 16The two is not hydrogen atom simultaneously, and the two is beyond the hydrogen atom time, adds up to take the carbon atom of their combinations to be no more than 4 as condition, represents independently hydrogen atom, C1～3 alkyl etc.
R 17Expression C1～4 alkyl, C3～6 cycloalkyl etc.
Patent documentation
Patent documentation 1: Japanese kokai publication sho 61-126065 communique
Patent documentation 2: Japanese kokai publication hei 1-131146 communique
Patent documentation 3: TOHKEMY 2005-517642 communique
Patent documentation 4: TOHKEMY 2006-507338 communique
Patent documentation 5: TOHKEMY 2006-507339 communique
Summary of the invention
Problem of the present invention provides novel noxious organism control agent, especially has excellent acaricidal activity and/or fungicidal activity, characteristic and excellent in safety and industrial favourable synthetic aryloxy carbamide compound or its salt of energy and contains it as miticide and/or the sterilant of effective constituent.
The inventor etc. conduct in-depth research in order to solve above-mentioned problem, found that aryloxy carbamide compound or its salt with ad hoc structure can become acaricidal activity and/or the fungicidal activity with excellence, and demonstrate the effective constituent of miticide and/or the sterilant of superperformance and high security.
The present invention is based on these opinions and finishes.
That is, the present invention comprises following content.
(1) aryloxy carbamide compound or its salt of formula (I) expression.
In the above-mentioned formula (I), Cy represents C6～10 aryl or heteroaryl.
X represents without replacement or substituent C1～6 alkyl is arranged; without replacing or substituent C3～8 cycloalkyl being arranged; without replacing or substituent C2～6 alkenyls being arranged; without replacing or substituent C2～6 alkynyls being arranged; hydroxyl; without replacing or substituent C1～6 alkoxyl groups being arranged; amino; without replacing or substituent C1～6 alkylaminos being arranged; without replacing or substituent C1～7 acyl groups being arranged; without replacing or substituent C1～6 alkoxy carbonyls being arranged; without replacing or substituent C1～6 alkyl sulphonyls being arranged; without replacing or substituent C1～6 alkoxyl group alkylsulfonyls being arranged; without replacing or substituent C6～10 aryl being arranged; without replacing or substituent heteroaryl being arranged; without replacing or substituent oxyimino C1～6 alkyl being arranged; nitro; cyano group; perhaps halogen atom.
N represents the number of the X on the Cy and is arbitrary integer in 0～5.N is 2 when above, and X can be mutually the same, also can differ from one another.In addition, n is 2 when above, and X can be together together forms ring with carbon atom or the nitrogen-atoms of bonding.
R 1Expression without replace or have substituent C1～6 alkyl, without replace or have substituent C2～6 alkenyls, without replace or substituent C2～6 alkynyls are arranged, without replacing or substituent C1～7 acyl groups being arranged or without replacing or substituent C1～6 alkoxy carbonyls being arranged.
Q represents the group that formula II, formula III or formula IV represent.
Figure GDA00003484046400042
In the above-mentioned formula II, * represents bonding position.R 2The expression hydrogen atom, without replace or have substituent C1～6 alkyl, without replace or have substituent C2～6 alkenyls, without replace or substituent C2～6 alkynyls are arranged, without replacing or substituent C1～7 acyl groups being arranged or without replacing or substituent C1～6 alkoxy carbonyls, R being arranged 1With R 2Can form together the nothing replacement or substituent C2～4 alkylidene groups are arranged.
R 3And R 4Represent independently of one another hydrogen atom, without replace or have substituent C1～6 alkyl, without replace or have substituent C2～6 alkenyls, without replace or have substituent C2～6 alkynyls, without replace or substituent C6～10 aryl are arranged, without replacing or substituent heteroaryl or cyano group being arranged.At this, R 3With R 4Can be together together form ring with the carbon atom of bonding.
R 5Expression is without replacement or substituent C1～6 alkyl are arranged; without replacing or substituent C3～8 cycloalkyl being arranged; without replacing or substituent C2～6 alkenyls being arranged; without replacing or substituent C2～6 alkynyls being arranged; without replacing or substituent C1～7 acyl groups being arranged; carboxyl; without replacing or substituent C1～6 alkoxy carbonyls being arranged; without replacing or substituent C2～6 alkenyl oxy carbonyls being arranged; without replacing or substituent C2～6 alkynyloxy base carbonyls being arranged; without replacing or substituent aminocarbonyl being arranged; without replacing or substituent C6～10 aryl being arranged; without replacing or substituent heteroaryl being arranged; without replacing or substituent oxyimino C1～6 alkyl being arranged; perhaps cyano group.
Figure GDA00003484046400051
In the above-mentioned formula III, * represents bonding position.R 6And R 7Independently of one another expression without replace or have substituent C1～6 alkyl, without replace or have substituent C3～8 cycloalkyl, without replace or have substituent C2～6 alkenyls, without replace or substituent C2～6 alkynyls are arranged, without replacing or substituent C6～10 aryl being arranged or without replacing or substituent heteroaryl being arranged.At this, R 6With R 7Can be together together form ring with the sulphur atom of bonding.
Figure GDA00003484046400052
In the above-mentioned formula IV, * represents bonding position.R 2With above-mentioned expression equivalent.R 8Expression without replace or have substituent C3～8 cycloalkyl, without replace or substituent C1～6 alkoxy carbonyls are arranged, without replacing or substituent C6～10 aryl being arranged or without replacing or substituent heteroaryl being arranged.
Z represents Sauerstoffatom or sulphur atom.
(2) the aryloxy carbamide compound of above-mentioned formula (I) expression is aryloxy carbamide compound or its salt that formula V represents.
Figure GDA00003484046400061
In the above-mentioned formula V, R 1～R 5, X, n and Z and above-mentioned expression equivalent.
(3) a kind of noxious organism control agent wherein, contains be selected from above-mentioned (1) or (2) described aryloxy carbamide compound or its salt at least a kind as effective constituent.
(4) a kind of miticide wherein, contains be selected from above-mentioned (1) or (2) described aryloxy carbamide compound or its salt at least a kind as effective constituent.
(5) a kind of sterilant wherein, contains be selected from above-mentioned (1) or (2) described aryloxy carbamide compound or its salt at least a kind as effective constituent.
Aryloxy carbamide compound of the present invention or its salt can be prevented and kill off the harmful organism that becomes problem aspect farm crop, the health.Especially effectively prevent and kill off mite class and/or pathogenic mushroom.
Embodiment
(aryloxy carbamide compound)
Aryloxy carbamide compound of the present invention is the compound of following formula (I) expression.
Figure GDA00003484046400062
(substituting group)
In the present invention, the term of " without what replace " means it only is the group that becomes parent nucleus.Should illustrate, the record that in this manual, does not have " substituting group is arranged " as long as no other explanation, is " without what replace " meaning during only with the title record of the group that becomes parent nucleus.
On the other hand, the term that " substituting group is arranged " means that any hydrogen atom in the group that becomes parent nucleus is replaced by the group of or different structure identical with parent nucleus.Therefore, " substituting group " is other group with the group bonding that becomes parent nucleus.Substituting group can be 1, also can be for more than 2.Substituting group more than 2 can be identical, also can be different.
The carbonatoms that terms such as " C1～6 " represents to become the group of parent nucleus is 1～6 etc.Do not comprise the carbonatoms that is present in the substituting group in this carbonatoms.For example, have oxyethyl group and be divided into C2 alkoxy C 4 alkyl as substituent butyl.
" substituting group " then is not particularly limited as long as chemically allow, have effect of the present invention.
As the group that can become " substituting group ", but the following group of illustration particularly.
The halogen atoms such as fluorine atom, chlorine atom, bromine atoms, iodine atom;
C1～6 alkyl such as methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl;
C3～8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, suberyl;
C2～6 alkenyls such as vinyl, 1-propenyl, 2-propenyl, 1-butylene base, crotyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butene base, 2-methyl-2-butene base, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl;
C3～8 cycloalkenyl groups such as 2-cyclopropenyl radical, 2-cyclopentenyl, 3-cyclohexenyl, 4-cyclooctene base;
Ethynyl, 1-proyl, 2-propynyl, ethyl acetylene base, 2-butyne base, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl, valerylene base, 3-pentynyl, 4-pentynyl, 1-methyl-2-butyne base, 2-methyl-3-pentynyl, 1-hexin base, 1,1-dimethyl-C2～6 alkynyls such as 2-butyne base;
C1～6 alkoxyl groups such as methoxyl group, oxyethyl group, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert.-butoxy;
C2～6 alkenyl oxies such as vinyl oxygen base, allyl group oxygen base, propenyl oxygen base, butenyl oxygen base;
C2～6 alkynyloxy the bases such as ethynyl oxygen base, propargyloxy;
The C6 such as phenyl, naphthyl～10 aryl;
C6～10 aryloxy such as phenoxy group, 1-naphthyloxy;
The C7 such as benzyl, styroyl～11 aralkyl;
C7～11 aralkyl oxies such as benzyl oxygen base, styroyl oxygen base;
C1～7 acyl groups such as formyl radical, ethanoyl, propionyl, benzoyl, cyclohexyl-carbonyl;
C1～7 acyloxy such as methanoyl, acetoxyl group, propionyloxy, benzoyl oxygen base, cyclohexyl-carbonyl oxygen base;
C1～6 alkoxy carbonyls such as methoxycarbonyl, ethoxy carbonyl, positive propoxy carbonyl, isopropoxy carbonyl, n-butoxy carbonyl, tert-butoxycarbonyl;
Carboxyl;
Hydroxyl;
Chloromethyl, chloroethyl, trifluoromethyl, 1, C1～6 haloalkyls such as 2-two chloro-n-propyls, 1-fluoro-normal-butyl, perfluor-n-pentyl;
C2～6 halogenated alkenyls such as 2-chloro-1-propenyl, 2-fluoro-1-butylene base;
C2～6 halo the alkynyls such as 4,4-, two chloro-ethyl acetylene bases, 4-fluoro-1-pentynyl, 5-bromo-valerylene base;
2-chloro-positive propoxy, 2, C1～6 halogenated alkoxies such as 3-dichloro butoxy;
C2～6 halogenated alkenyl oxies such as 2-Chloroallyl oxygen base, 3-bromobutene base oxygen base;
C6～10 halogenated aryls such as 4-chloro-phenyl-, 4-fluorophenyl, 2,4 dichloro benzene base;
C6～10 halo the aryloxy such as 4-fluorophenoxy, 4-chloro-1-naphthyloxy;
The halogens such as chloracetyl, trifluoroacetyl group, tribromo-acetyl base, 4-chlorobenzene formacyl replace C1～7 acyl groups;
Cyano group; Nitro; Amino;
C1～6 alkylaminos such as methylamino-, dimethylamino, diethylin;
The C6 such as anilino, naphthylamino～10 arylaminos;
C7～11 aryl alkyl aminos such as benzylamino, phenyl ethylamino;
C1～7 acyl aminos such as formamido group, kharophen, propionamido, butyrylamino, sec.-propyl carbonylamino, benzamido;
C1～6 alkoxycarbonyl aminos such as methoxycarbonyl is amino, ethoxy carbonyl is amino, positive propoxy carbonylamino, isopropoxy carbonyl amino;
Aminocarbonyl, carbonyl dimethyl ammonium, phenylamino carbonyl, N-phenyl-nothings such as N-methyl aminocarbonyl replace or substituent aminocarbonyl are arranged;
Iminomethyl, (1-imino-) ethyl, (1-the imino-)-imino-C1 such as n-propyl～6 alkyl;
Oxyimino C1～6 alkyl such as oxyimino methyl, (1-oxyimino) ethyl, (1-oxyimino) propyl group;
Sulfydryl;
C1～6 alkyl the sulfenyls such as methylthio group, ethylmercapto group, n-propyl sulfenyl, sec.-propyl sulfenyl, normal-butyl sulfenyl, isobutyl-sulfenyl, sec-butyl sulfenyl, tertiary butyl sulfenyl;
C2～6 alkenyl thios such as vinyl sulfenyl, allyl group sulfenyl;
C2～6 alkynyl the sulfenyls such as ethynyl sulfenyl, propargyl sulfenyl;
C6～10 artyl sulfos such as thiophenyl, naphthalene sulfenyl;
The heteroaryl sulfenyls such as thiazolyl sulfenyl, pyridyl sulfenyl;
C7～11 aromatic alkyl sulfurios such as benzyl sulfenyl, styroyl sulfenyl;
(C1～6 alkyl sulfenyls) carbonyls such as (methylthio group) carbonyl, (ethylmercapto group) carbonyl, (n-propyl sulfenyl) carbonyl, (sec.-propyl sulfenyl) carbonyl, (normal-butyl sulfenyl) carbonyl, (isobutyl-sulfenyl) carbonyl, (sec-butyl sulfenyl) carbonyl, (tertiary butyl sulfenyl) carbonyl;
C1～6 alkyl sulphinyls such as methylsulfinyl, ethyl sulfinyl, tertiary butyl sulfinyl;
C2～6 alkenyl the sulfinyls such as allyl group sulfinyl;
C2～6 alkynyl the sulfinyls such as propargyl sulfinyl;
C6～10 aryl sulfonyl kias such as phenyl sulfinyl;
The heteroaryl sulfinyls such as thiazolyl sulfinyl, pyridyl sulfinyl;
C7～11 aralkyl sulfinyls such as benzyl sulfinyl, styroyl sulfinyl;
C1～6 alkyl sulphonyls such as methyl sulphonyl, ethylsulfonyl, tertiary butyl alkylsulfonyl;
C2～6 alkenyl the alkylsulfonyls such as allyl group alkylsulfonyl;
C2～6 alkynyl the alkylsulfonyls such as propargyl alkylsulfonyl;
The C6 such as phenyl sulfonyl～10 aryl sulfonyls;
The heteroarylsulfonyl such as thiazolyl alkylsulfonyl, pyridyl sulfonyl;
C7～11 aralkyl the alkylsulfonyls such as benzyl alkylsulfonyl, styroyl alkylsulfonyl;
Pyrryl, furyl, thienyl, imidazolyl, pyrazolyl,
Figure GDA00003484046400101
Azoles base, different
Figure GDA00003484046400102
Azoles base, thiazolyl, isothiazolyl, triazolyl,
Figure GDA00003484046400103
5 yuan of ring heteroaryls such as di azoly, thiadiazolyl group, tetrazyl;
6 yuan of ring heteroaryls such as pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, triazinyl;
Indyl, benzofuryl, benzothienyl, benzimidazolyl-, benzo
Figure GDA00003484046400104
The condensed ring heteroaryls such as azoles base, benzothiazolyl, quinolyl, isoquinolyl, quinoxalinyl;
The saturated heterocyclyls such as aziridinyl, Oxyranyle, pyrrolidyl, tetrahydrofuran base, piperidyl, piperazinyl, morpholine;
Three C1 such as trimethyl silyl, triethylsilyl, t-butyldimethylsilyl～6 alkyl replace silyl;
The triphenyl silyl;
In addition, these " substituting groups " can further have other " substituting group ".
〔Cy〕
In the formula (I), Cy represents C6～10 aryl or heteroaryl.
" C6～10 aryl " can be monocycle or encircle in many rings that bonding each other forms any.Polyaromatic is as long as at least one ring is aromatic nucleus, and all the other rings can be in saturated fat ring, unsaturated alicyclic ring or the aromatic nucleus any.As C6～10 aryl, but illustration phenyl, naphthyl,
Figure GDA00003484046400111
Base, indenyl, indanyl, tetrahydro naphthyl etc.
" heteroaryl " is also to contain 1～4 heteroatoms being selected from nitrogen-atoms, Sauerstoffatom and the sulphur atom as 5～10 yuan of aryl of the atom that consists of ring except carbon atom.In this case, can be that monocycle or ring condense the many rings that form each other.
As heteroaryl, can enumerate illustrative 5 yuan of ring heteroaryls in the above-mentioned substituting group, 6 yuan of ring heteroaryls, condensed ring heteroaryl etc.
Among these, Cy is preferably phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, more preferably phenyl.
〔X〕
In the formula (I), X represents without replacement or substituent C1～6 alkyl is arranged; without replacing or substituent C3～8 cycloalkyl being arranged; without replacing or substituent C2～6 alkenyls being arranged; without replacing or substituent C2～6 alkynyls being arranged; hydroxyl; without replacing or substituent C1～6 alkoxyl groups being arranged; amino; without replacing or substituent C1～6 alkylaminos being arranged; without replacing or substituent C1～7 acyl groups being arranged; without replacing or substituent C1～6 alkoxy carbonyls being arranged; without replacing or substituent C1～6 alkyl sulphonyls being arranged; without replacing or substituent C1～6 alkoxyl group alkylsulfonyls being arranged; without replacing or substituent C6～10 aryl being arranged; without replacing or substituent heteroaryl being arranged; without replacing or substituent oxyimino C1～6 alkyl being arranged; nitro; cyano group; perhaps halogen atom.
N represents the number of the X on the Cy and is arbitrary integer in 0～5.N is 2 when above, and X can be mutually the same, also can differ from one another.In addition, n is 2 when above, and X can be together together forms ring with carbon atom or the nitrogen-atoms of bonding.
" C1～6 alkyl " among the X can be straight chain, also can be side chain.As alkyl, but illustration methyl, ethyl, n-propyl, normal-butyl, n-pentyl, n-hexyl, sec.-propyl, isobutyl-, sec-butyl, the tertiary butyl, isopentyl, neo-pentyl, 2-methyl butyl, 2,2-dimethyl propyl, isohexyl etc.
As " substituent alkyl is arranged ", but illustration
C3～8 cycloalkyl C1～6 alkyl such as cyclopropyl methyl, 2-cyclopropyl ethyl, cyclopentyl-methyl, 2-cyclohexyl ethyl, 2-ring octyl group ethyl;
Methyl fluoride, chloromethyl, brooethyl, difluoromethyl, dichloromethyl, two brooethyls, trifluoromethyl, trichloromethyl, trisbromomethyl, 2,2,2-trifluoroethyl, 2,2,2-three chloroethyls, pentafluoroethyl group, 4-fluorine butyl, 4-chlorobutyl, 3,3,3-trifluoro propyl, 2,2,2-three fluoro-1-trifluoromethyl ethyls, perfluoro hexyl, perchloro-hexyl, perfluoro capryl, perchloro-octyl group, 2, C1～6 haloalkyls such as 4,6-trichlorine hexyl;
Hydroxyl C1～6 alkyl such as hydroxymethyl, 2-hydroxyethyl;
C1～6 alkoxy Cs, 1～6 alkyl such as methoxymethyl, ethoxyl methyl, methoxy ethyl, ethoxyethyl group, methoxyl group n-propyl, ethoxyl methyl, ethoxyethyl group, n-propoxymethyl, isopropoxy ethyl, sec-butoxy methyl, tert.-butoxy ethyl;
C2～6 alkenyl oxy C1～6 alkyl such as vinyl oxygen ylmethyl, allyl group oxygen ylmethyl, propenyl oxygen ylmethyl, butenyl oxygen ylmethyl;
Pyridine-heteroaryloxy C1～6 alkyl such as 2-base oxygen ylmethyl;
C1～7 acyl groups such as formyl radical, ethanoyl, propionyl;
C1～7 acyloxy C1～6 alkyl such as methanoyl methyl, acetoxy-methyl, 2-acetoxyl group ethyl, propionyloxy methyl, propionyloxy ethyl;
The carboxyl such as carboxymethyl, propyloic C1～6 alkyl;
C1～6 alkoxy carbonyl C1～6 alkyl such as methoxycarbonyl methyl, ethoxy carbonyl methyl, positive propoxy carbonyl methyl, isopropoxy carbonyl methyl;
C1～7 acyl amino C1～6 alkyl such as formamido-methyl, acetamidomethyl, 2-acetamido ethyl, propionyl amino methyl, propionyl amino-ethyl;
C1～6 alkyl amino-carbonyl C1～6 alkyl such as methylamino carbonyl methyl, ethylamino carbonyl methyl, isopropylamino carbonyl methyl, tertiary butyl amino carbonyl methyl, sec-butyl amino carbonyl methyl, n-pentyl amino carbonyl methyl;
C1～6 alkoxycarbonyl amino C1～6 alkyl such as methoxycarbonyl amino methyl, ethoxy carbonyl amino methyl, isopropoxy carbonyl amino methyl, tert-butoxycarbonyl amino methyl, sec-butyl oxygen base carbonylamino methyl, n-pentyl oxygen base carbonylamino methyl;
The C7 such as benzyl, styroyl～11 aralkyl;
The C6 such as benzene carbon amide ylmethyl～10 aryl-amino-carbonyl C1～6 alkyl etc.
As " C3～8 cycloalkyl " among the X but illustration cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, suberyl etc.
As " C2～6 alkenyls " among the X, but illustration vinyl, 1-propenyl, 2-propenyl, 1-butylene base, crotyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butene base, 2-methyl-2-butene base, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl etc.
As " substituent C2～6 alkenyls are arranged ", but C2～6 halogenated alkenyls such as illustration 2-chloro-1-propenyl, 2-fluoro-1-butylene base.
As " C2～6 alkynyls " among the X, but illustration ethynyl, 1-proyl, 2-propynyl, ethyl acetylene base, 2-butyne base, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl, valerylene base, 3-pentynyl, 4-pentynyl, 1-methyl-2-butyne base, 2-methyl-3-pentynyl, 1-hexin base, 1,1-dimethyl-2-butyne base etc.
As " substituent C2～6 alkynyls are arranged ", but illustration 4, the C2～6 halo alkynyls such as 4-two chloro-ethyl acetylene bases, 4-fluoro-1-pentynyl, 5-bromo-valerylene base.
As " C1～6 alkoxyl groups " among the X, but illustration methoxyl group, oxyethyl group, positive propoxy, n-butoxy, n-pentyl oxygen base, n-hexyl oxygen base, isopropoxy, isobutoxy, sec-butoxy, tert.-butoxy, isohexyl oxygen base etc.
As " substituent C1～6 alkoxyl groups are arranged ", but illustration chlorine methoxyl group, dichloro methoxyl group, difluoro-methoxy, trichlorine methoxyl group, trifluoromethoxy, 1-fluorine oxyethyl group, 1,1-difluoroethoxy, 2,2, the C1 such as 2-trifluoro ethoxy, five fluorine oxyethyl groups～6 halogenated alkoxies etc.
As " C1～6 alkylaminos " among the X, but illustration methylamino-, dimethylamino, diethylin etc.
As " C1～7 acyl groups " among the X, but illustration formyl radical, ethanoyl, propionyl, benzoyl etc.
As " substituent C1～7 acyl groups are arranged ", but the halogens such as illustration chloracetyl, trifluoroacetyl group, tribromo-acetyl base, 4-chlorobenzene formacyl replace C1～7 acyl groups.
As " C1～6 alkoxy carbonyls " among the X, but illustration methoxycarbonyl, ethoxy carbonyl, positive propoxy carbonyl, isopropoxy carbonyl etc.
As " substituent C1～6 alkoxy carbonyls are arranged ", but illustration
Cyclo propyl methoxy carbonyl, cyclobutyl methoxy base carbonyl, cyclopentyl methoxycarbonyl, cyclohexyl methoxycarbonyl, 2-methyl cyclo propyl methoxy carbonyl, 2, C3～8 cycloalkyl C1～6 alkoxy carbonyls such as 3-dimethyl cyclo propyl methoxy carbonyl, 2-chlorine cyclo propyl methoxy carbonyl, 2-cyclopropyl ethoxy carbonyl;
Fluorine methoxycarbonyl, chlorine methoxycarbonyl, bromine methoxycarbonyl, difluoro-methoxy carbonyl, dichloro methoxycarbonyl, dibromo methoxycarbonyl, trifluoromethoxy carbonyl, trichlorine methoxycarbonyl, tribromo methoxycarbonyl, 2,2,2-trifluoro ethoxy carbonyl, 2,2,2-trichlorine ethoxy carbonyl, five fluorine ethoxy carbonyls, 4-fluorine butoxy carbonyl, 3,3,3-trifluoro propoxycarbonyl, 2, C1～6 halo alkoxy carbonyls such as 2,2-, three fluoro-1-trifluoromethyl ethoxy carbonyls, perfluoro hexyl oxygen base carbonyl etc.
As " C1～6 alkyl sulphonyls " among the X, but illustration methyl sulphonyl, ethylsulfonyl, tertiary butyl alkylsulfonyl etc.
As " C1～6 alkoxyl group alkylsulfonyls " among the X, but illustration methoxyl group alkylsulfonyl, oxyethyl group alkylsulfonyl, tert.-butoxy alkylsulfonyl etc.
As " C6～10 aryl " and " heteroaryl " among the X, can enumerate with above-mentioned Cy in illustrative those identical C6～10 aryl and heteroaryl.
As " C6～10 aryl " among the X and the substituting group on " heteroaryl ", but illustration
The halogen atoms such as fluorine atom, chlorine atom, bromine atoms, iodine atom;
C1～6 alkyl such as methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl;
Chloromethyl, chloroethyl, trifluoromethyl, 1, C1～6 haloalkyls such as 2-two chloro-n-propyls, 1-fluoro-normal-butyl, perfluor-n-pentyl;
Cyano group etc.
As " the oxyimino C1～6 alkyl " among the X, but illustration oxyimino methyl, (1-oxyimino) ethyl, (1-oxyimino) propyl group etc.
As " substituent oxyimino C1～6 alkyl are arranged ", but C1～6 Alkoximino C1～6 alkyl such as illustration methoxyimino methyl, (1-methoxyimino) ethyl, (1-methoxyimino) propyl group, ethoxy imino methyl, (1-ethoxy imino) ethyl, (1-ethoxy imino) propyl group; C3～8 cycloalkyl C1～6 Alkoximino C1～6 alkyl such as (1-cyclo propyl methoxy imino-) ethyl; C7～11 aralkyl oxy imino-C1～6 alkyl such as benzyl oxygen base iminomethyl, (1-benzyl oxygen base imino-) ethyl etc.
As " halogen atom " among the X, but illustration fluorine atom, chlorine atom, bromine atoms, iodine atom etc.
N is 2 when above, the ring that forms together as carbon atom or nitrogen-atoms with the X bonding, but illustration cyclopentenes ring, cyclohexene ring, 3,4-dihydro-2H-pyranoid ring, 3,4-dihydro-2H-thiapyran ring, 3,4-dihydro-2H-thiapyran, 1,1-dioxide ring etc.
〔R 1〕
In the formula (I), R 1Expression without replace or have substituent C1～6 alkyl, without replace or have substituent C2～6 alkenyls, without replace or substituent C2～6 alkynyls are arranged, without replacing or substituent C1～7 acyl groups being arranged or without replacing or substituent C1～6 alkoxy carbonyls being arranged.
As R 1In " C1～6 alkyl ", " C2～6 alkenyls ", " C2～6 alkynyls ", " C1～7 acyl groups " and " C1～6 alkoxy carbonyls ", can enumerate with above-mentioned X in illustrative those identical groups.
〔Q〕
In the formula (I), Q represents the group that formula II, formula III or formula IV represent.
Figure GDA00003484046400151
In the formula II, * represents bonding position.
〔R 2〕
In the formula II, R 2The expression hydrogen atom, without replace or have substituent C1～6 alkyl, without replace or have substituent C2～6 alkenyls, without replace or substituent C2～6 alkynyls are arranged, without replacing or substituent C1～7 acyl groups being arranged or without replacing or substituent C1～6 alkoxy carbonyls, R being arranged 1With R 2Can form together the nothing replacement or substituent C2～4 alkylidene groups are arranged.
As R 2In " C1～6 alkyl ", " C2～6 alkenyls ", " C2～6 alkynyls ", " C1～7 acyl groups " and " C1～6 alkoxy carbonyls ", can enumerate with above-mentioned X in illustrative those identical groups.
As R 1With R 2" without replacing or substituent C2～4 alkylidene groups being arranged " that forms together, but illustration ethylidene, propylidene (trimethylene) etc.
〔R 3、R 4〕
In the formula II, R 3And R 4Represent independently of one another hydrogen atom, without replace or have substituent C1～6 alkyl, without replace or have substituent C2～6 alkenyls, without replace or have substituent C2～6 alkynyls, without replace or substituent C6～10 aryl are arranged, without replacing or substituent heteroaryl or cyano group being arranged.At this, R 3And R 4Can be together together form ring with the carbon atom of bonding.
As R 3And R 4In " C1～6 alkyl ", " C2～6 alkenyls " and " C2～6 alkynyls ", can enumerate with above-mentioned X in illustrative those identical groups.
As R 3And R 4In " C6～10 aryl " and " heteroaryl ", can enumerate with above-mentioned Cy in illustrative those identical groups.
As R 3And R 4" ring " that together forms with the carbon atom of bonding together, but illustration cyclopropane ring, tetramethylene ring, pentamethylene ring, cyclohexane ring, oxyethane ring etc.
〔R 5〕
In the formula II, R 5Expression is without replacement or substituent C1～6 alkyl are arranged; without replacing or substituent C3～8 cycloalkyl being arranged; without replacing or substituent C2～6 alkenyls being arranged; without replacing or substituent C2～6 alkynyls being arranged; without replacing or substituent C1～7 acyl groups being arranged; carboxyl; without replacing or substituent C1～6 alkoxy carbonyls being arranged; without replacing or substituent C2～6 alkenyl oxy carbonyls being arranged; without replacing or substituent C2～6 alkynyloxy base carbonyls being arranged; without replacing or substituent aminocarbonyl being arranged; without replacing or substituent C6～10 aryl being arranged; without replacing or substituent heteroaryl being arranged; without replacing or substituent oxyimino C1～6 alkyl being arranged; perhaps cyano group.
As R 5In " C1～6 alkyl ", " C3～8 cycloalkyl ", " C2～6 alkenyls ", " C2～6 alkynyls ", " C1～7 acyl groups " and " C1～6 alkoxy carbonyls ", can enumerate with above-mentioned X in illustrative those identical groups.
As R 5In " C6～10 aryl ", but illustration phenyl, naphthyl,
Figure GDA00003484046400171
Base, indenyl, indanyl, tetrahydro naphthyl etc.
As R 5In " heteroaryl ", but illustration pyrryl, furyl, thienyl, imidazolyl, pyrazolyl,
Figure GDA00003484046400172
Azoles base, different Azoles base, thiazolyl, isothiazolyl, triazolyl,
Figure GDA00003484046400174
The heteroaryl of 5 yuan of rings such as di azoly, thiadiazolyl group, tetrazyl;
The heteroaryl of 6 yuan of rings such as pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, triazinyl;
Indyl, benzofuryl, benzothienyl, benzimidazolyl-, benzo
Figure GDA00003484046400175
The condensed ring heteroaryls such as azoles base, benzothiazolyl, quinolyl, isoquinolyl, quinoxalinyl;
Pyrrolinyl, imidazolinyl, pyrazolinyl,
Figure GDA00003484046400176
The unsaturated 5 yuan of heterocycles of part such as azoles quinoline base, thiazolinyl etc.
Preferably illustration phenyl, pyridyl etc.
As R 5In " C6～10 aryl " and the substituting group on " heteroaryl ", but illustration
The halogen atoms such as fluorine atom, chlorine atom, bromine atoms, iodine atom;
C1～6 alkyl such as methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl;
Chloromethyl, chloroethyl, trifluoromethyl, 1, C1～6 haloalkyls such as 2-dichloro n-propyl, 1-fluorine normal-butyl, perfluor n-pentyl;
Cyano group etc.
As " C2～6 alkenyl oxy carbonyls ", but illustration vinyl oxygen base carbonyl, 1-methyl-2-propenyl oxygen base carbonyl, 2-methyl-1-propylene base oxygen base carbonyl etc.
As " C2～6 alkynyloxy base carbonyls ", but illustration ethynyl oxygen base carbonyl, propargyloxy carbonyl, 1-methyl propargyloxy carbonyl, 2-butyne base oxygen base carbonyl etc.
As " substituent aminocarbonyl is arranged ", but C1～6 alkyl amino carbonyls such as illustration methyl aminocarbonyl, ethyl aminocarbonyl, sec.-propyl aminocarbonyl, tertiary butyl aminocarbonyl, sec-butyl aminocarbonyl, n-pentyl aminocarbonyl; Two C1～6 alkyl amino carbonyls such as carbonyl dimethyl ammonium, diethyl amino carbonyl; C3～8 cycloalkyl the aminocarbonyls such as cyclopropyl aminocarbonyl, cyclopentyl aminocarbonyl, cyclohexyl aminocarbonyl; C2～6 alkynyl the aminocarbonyls such as 2-propynyl aminocarbonyl; Phenylamino carbonyl, N-phenyl-N-methyl aminocarbonyl; C1～6 alkoxy Cs, 1～6 alkyl amino carbonyls such as methoxy ethyl aminocarbonyl; C1～6 haloalkyl the aminocarbonyls such as 2,2,2-trifluoroethyl aminocarbonyl; C3～8 cycloalkyl C1～6 alkyl amino carbonyls such as cyclopropyl methyl aminocarbonyl; C7～11 alkyl aryl ammonium the carbonyls such as benzyl aminocarbonyl; 1 replacement-ring-type aminocarbonyl such as piperidin-1-yl carbonyl etc.
As " oxyimino C1～6 alkyl ", but illustration oxyimino methyl, (1-oxyimino) ethyl, (1-oxyimino) propyl group etc.
As " substituent oxyimino C1～6 alkyl are arranged ", but C1～6 Alkoximino C1～6 alkyl such as illustration methoxyimino methyl, (1-methoxyimino) ethyl, (1-methoxyimino) propyl group, ethoxy imino methyl, (1-ethoxy imino) ethyl, (1-ethoxy imino) propyl group; C3～8 cycloalkyl C1～6 Alkoximino C1～6 alkyl such as (1-cyclo propyl methoxy imino-) ethyl; C7～11 aralkyl oxy imino-C1～6 alkyl such as benzyl oxygen base iminomethyl, (1-benzyl oxygen base imino-) ethyl etc.
Figure GDA00003484046400181
In the formula III, * represents bonding position.
〔R 6、R 7〕
In the formula III, R 6And R 7Independently of one another expression without replace or have substituent C1～6 alkyl, without replace or have substituent C3～8 cycloalkyl, without replace or have substituent C2～6 alkenyls, without replace or substituent C2～6 alkynyls are arranged, without replacing or substituent C6～10 aryl being arranged or without replacing or substituent heteroaryl being arranged.At this, R 6And R 7Can be together together form ring with the sulphur atom of bonding.
As R 6And R 7In " C1～6 alkyl ", " C3～8 cycloalkyl ", " C2～6 alkenyls " and " C2～6 alkynyls ", can enumerate with above-mentioned X in illustrative those identical groups.
As R 6And R 7In " C6～10 aryl " and " heteroaryl ", can enumerate with above-mentioned Cy in illustrative those identical groups.
As R 6And R 7In " C6～10 aryl " and the substituting group on " heteroaryl ", but illustration
The halogen atoms such as fluorine atom, chlorine atom, bromine atoms, iodine atom;
C1～6 alkyl such as methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl;
Chloromethyl, chloroethyl, trifluoromethyl, 1, C1～6 haloalkyls such as 2-dichloro n-propyl, 1-fluorine normal-butyl, perfluor n-pentyl;
Cyano group etc.
As R 6And R 7" ring " that together forms with the sulphur atom of bonding together, but illustration tetramethylene sulfide ring, tetrahydric thiapyran ring, oxathiane ring etc.
In the above-mentioned formula IV, * represents bonding position.R 2Represent the meaning same as described above.R 8Expression without replace or have substituent C3～8 cycloalkyl, without replace or substituent C1～6 alkoxy carbonyls are arranged, without replacing or substituent C6～10 aryl being arranged or without replacing or substituent heteroaryl being arranged.
As R 8In " C3～8 cycloalkyl ", can enumerate with above-mentioned X in illustrative those identical groups.
As " substituent C3～8 cycloalkyl are arranged ", but the C6 such as illustration 2-phenycyclopropyl～10 aryl C3～8 cycloalkyl etc.
As R 8In " C1～6 alkoxy carbonyls ", can enumerate with above-mentioned X in illustrative those identical groups.
As R 8In " C6～10 aryl ", but illustration phenyl, naphthyl,
Figure GDA00003484046400201
Base, indenyl, indanyl, tetrahydro naphthyl etc.
As R 8In " heteroaryl ", but illustration pyrryl, furyl, thienyl, imidazolyl, pyrazolyl,
Figure GDA00003484046400202
Azoles base, different
Figure GDA00003484046400203
Azoles base, thiazolyl, isothiazolyl, triazolyl, The heteroaryl of 5 yuan of rings such as di azoly, thiadiazolyl group, tetrazyl;
The heteroaryl of 6 yuan of rings such as pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, triazinyl;
Indyl, benzofuryl, benzothienyl, benzimidazolyl-, benzo
Figure GDA00003484046400205
The condensed ring heteroaryls such as azoles base, benzothiazolyl, quinolyl;
The fractional saturation annelated heterocycles such as tetrahydric quinoline group etc.
As R 8In " C6～10 aryl " and the substituting group on " heteroaryl ", but illustration
The halogen atoms such as fluorine atom, chlorine atom, bromine atoms, iodine atom;
C1～6 alkyl such as methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl;
Chloromethyl, chloroethyl, trifluoromethyl, 1, C1～6 haloalkyls such as 2-two chloro-n-propyls, 1-fluorine normal-butyl, perfluor n-pentyl;
Cyano group etc.
〔Z〕
In the formula (I), Z represents Sauerstoffatom or sulphur atom.Be preferably Sauerstoffatom.
(the aryloxy carbamide compound that formula V represents)
Among the aryloxy carbamide compound involved in the present invention, the Cy in the preferred formula (I) is that phenyl and Q are the compounds of the group that represents of formula II.That is, the aryloxy carbamide compound that represents of preferred formula V.
Figure GDA00003484046400206
In the above-mentioned formula V, R 1～R 5, X, n and Z represent the meaning same as described above.
(salt of aryloxy carbamide compound)
The salt of aryloxy carbamide compound of the present invention so long as the salt of allowing on the agricultural Horticulture then be not particularly limited.Such as the salt that can enumerate the mineral acids such as hydrochloric acid, sulfuric acid; The organic acid such as acetic acid, lactic acid salt; The alkali-metal salt such as lithium, sodium, potassium; The salt of the alkaline-earth metal such as calcium, magnesium; The salt of the transition metal such as iron, copper; The salt of the organic basess such as ammonia, triethylamine, tributylamine, pyridine, hydrazine etc.The salt of aryloxy carbamide compound can obtain according to known method.
(manufacture method)
Then, the manufacture method of aryloxy carbamide compound of the present invention described.
1) as the first manufacture method, but the manufacture method shown in the following scheme of illustration.
Figure GDA00003484046400211
A) alkali exists the lower aryloxy amine compound that makes phenyl chloroformate and formula (1) expression (below, be sometimes referred to as " compound (1) ") to react, the diester compound that acquisition formula (2) represents (below, be sometimes referred to as " compound (2) ").Then, it is taken off Bocization in the presence of trifluoroacetic acid, the N-aryloxy phenyl carbamate compound of manufacturing formula (3) expression (below, be sometimes referred to as " compound (3) ").Should illustrate, in formula (1)～formula (3), X, n and Cy and above-mentioned same meaning.）
With respect to (1) 1 mole of compound, the usage quantity of phenyl chloroformate is generally 1～2 mole, is preferably 1.0～1.2 moles.
This reaction also can be carried out in the presence of alkali non-, but preferably carries out in the presence of alkali.As alkali, can enumerate pyridine, triethylamine, potassium hydroxide etc.With respect to (1) 1 mole of compound, the usage quantity of alkali is generally 1～2 mole.
This reaction can be carried out in solvent.Solvent is so long as to reacting for the solvent of inertia, just be not particularly limited.For example can enumerate two
Figure GDA00003484046400221
Alkane, 1, the ether series solvents such as 2-glycol dimethyl ether, tetrahydrofuran (THF); The aromatic hydrocarbon series solvents such as toluene, benzene, dimethylbenzene; The aliphatic hydrocarbon series solvents such as Skellysolve A, normal hexane, normal heptane; Methylene dichloride, chloroform, tetracol phenixin, 1, the halohydrocarbon series solvents such as 2-ethylene dichloride; The acid amides series solvents such as DMF, N,N-dimethylacetamide, N-Methyl pyrrolidone; The nitrile such as acetonitrile, cyanobenzene series solvent; And by these two or more mixed solvents that consist of etc.The usage quantity of solvent is not particularly limited, but with respect to compound (1) 1g, is generally 1～100ml.
Temperature of reaction is the temperature range from-20 ℃ to the solvent boiling point that uses.Reaction times is determined by reaction scale, but is generally several minutes～tens of hours.
Then, taking off the Bocization reaction carries out in the presence of acid catalyst.As the acid of using, can enumerate the mineral acids such as hydrochloric acid, sulfuric acid, nitric acid; Acetic acid, trifluoroacetic acid, methylsulfonic acid, tosic acid etc., but preferred trifluoroacetic acid.With respect to (2) 1 moles of compounds, the usage quantity of acid is generally 1～20 mole.
This reaction is carried out in solvent.The solvent that uses is so long as to the solvent of reaction as inertia, just be not particularly limited.Can enumerate and as carry out for the manufacture of the solvent of compound (2) illustrative solvent phase with solvent.The usage quantity of solvent is not particularly limited, but with respect to compound (2) 1g, is generally 1～100ml.
Temperature of reaction is the temperature range from room temperature to the solvent boiling point that uses.Reaction times is determined by reaction scale, but is generally several minutes～tens of hours.
B) compound (below, be sometimes referred to as " compound (4) ") of formula (4) expression is reacted with compound (3), the aryloxy carbamide compound of manufacturing formula (5) expression (below, be sometimes referred to as " compound (5) ").At this; compound (4) be formula (4-1) expression amine compound (below; be sometimes referred to as " compound (4-1) "), the sulfinyl group with imine moiety of formula (4-2) expression (below; be sometimes referred to as " compound (4-2) ") or the amine compound of formula (4-3) expression (below, be sometimes referred to as " compound (4-3) ") in any.(in formula (4) and the formula (5), X, n, Q and Cy and above-mentioned same meaning.In formula (4-1), formula (4-2) and the formula (4-3), R 2～R 8With above-mentioned same meaning.）
With respect to (3) 1 moles of compounds, the usage quantity of compound (4) is generally 1～2 mole, is preferably 1.0～1.2 moles.
This reaction is carried out in solvent.The solvent that uses is so long as to the solvent of reaction as inertia, just be not particularly limited.Can enumerate and as carry out for the manufacture of the solvent of compound (2) illustrative solvent phase with solvent.The usage quantity of solvent is not particularly limited, but with respect to compound (3) 1g, is generally 1～100ml.
In addition, when reacting with compound (4-2), preferably in the presence of alkali, carry out.As alkali, can enumerate pyridine, triethylamine, potassium hydroxide etc.With respect to (3) 1 moles of compounds, the usage quantity of alkali is generally 1～2 mole.
Temperature of reaction is the temperature range from room temperature to the solvent boiling point that uses.Reaction times is determined by reaction scale, but is generally several minutes～tens of hours.
B) alkali exists the lower iodide that make formula (6) expression (below, be sometimes referred to as " compound (6) ") to react with compound (5), the aryloxy carbamide compound of manufacturing objective thing formula (7) expression (below, be sometimes referred to as " compound (7) ").(in formula (6) and the formula (7), X, n, Q, R 1, and Cy and above-mentioned same meaning.）
With respect to (5) 1 moles of compounds, the usage quantity of compound (6) is generally 1～2 mole, is preferably 1.0～1.2 moles.
As alkali, can enumerate pyridine, triethylamine, potassium hydroxide, calcium carbonate etc.With respect to (5) 1 moles of compounds, the usage quantity of alkali is generally 1～2 mole.
This reaction is carried out in solvent.The solvent that uses is so long as to the solvent of reaction as inertia, just be not particularly limited.Can enumerate and as carry out for the manufacture of the solvent of compound (2) illustrative solvent phase with solvent.The usage quantity of solvent is not particularly limited, but with respect to compound (5) 1g, is generally 1～100ml.
Temperature of reaction is the temperature range from-20 ℃ to the solvent boiling point that uses.Reaction times is determined by reaction scale, but is generally several minutes～tens of hours.
2) as second manufacture method, but the manufacture method shown in the following scheme of illustration.
Figure GDA00003484046400241
A) make compound (4) with can by the N-benzyl oxygen aminocarbamic acid phenyl ester of known method preparation (below, be sometimes referred to as " compound (8) ") react, the benzyl oxygen base carbamide compound of manufacturing formula (9) expression (below, be sometimes referred to as " compound (9) ").(in the formula (9), Q and above-mentioned same meaning.）
With respect to (8) 1 moles of compounds, the usage quantity of compound (4) is generally 1～2 mole, is preferably 1.0～1.2 moles.
This reaction is carried out in solvent.The solvent that uses is so long as to the solvent of reaction as inertia, just be not particularly limited.Can enumerate and as carry out for the manufacture of the solvent of compound (2) illustrative solvent phase with solvent.The usage quantity of solvent is not particularly limited, but with respect to compound (8) 1g, is generally 1～100ml.
In addition, make compound (4-2) when reacting, preferably in the presence of alkali, carry out.As alkali, can enumerate pyridine, triethylamine, potassium hydroxide etc.With respect to (8) 1 moles of compounds, the usage quantity of alkali is generally 1～2 mole.
Temperature of reaction is the temperature range from room temperature to the solvent boiling point that uses.Reaction times is determined by reaction scale, but is generally several minutes～tens of hours.
B) make compound (6) and compound (9) react the formula of making (10) expression benzyl oxygen base carbamide compound (below, be sometimes referred to as " compound (10) ") after, carry out debenzylation by the contact reduction, the oxygen base carbamide compound of manufacturing formula (11) expression (below, be sometimes referred to as " compound (11) ").(in formula (10) and the formula (11), Q and R 1With above-mentioned same meaning.）
With respect to (9) 1 moles of compounds, the usage quantity of compound (6) is generally 1～2 mole, is preferably 1.0～1.2 moles.
This reaction is carried out in solvent.The solvent that uses is so long as to the solvent of reaction as inertia, just be not particularly limited.Can enumerate and as carry out for the manufacture of the solvent of compound (2) illustrative solvent phase with solvent.The usage quantity of solvent is not particularly limited, but with respect to compound (9) 1g, is generally 1～100ml.
Temperature of reaction is the temperature range from-20 ℃ to the solvent boiling point that uses.Reaction times is determined by reaction scale, but is generally several minutes～tens of hours.
Then, debenzylating reaction is undertaken by the contact hydrogen reduction that utilizes palladium catalyst etc.As the palladium catalyst that uses, can enumerate palladium black, palladium carbon etc.With respect to (10) 1 moles of compounds, the usage quantity of palladium catalyst is generally 0.01～0.1 mole.
This reaction is carried out in solvent.The solvent that uses is so long as to the solvent of reaction as inertia, just be not particularly limited.Can enumerate and as carry out for the manufacture of the solvent of compound (2) illustrative solvent phase with solvent.Other also can enumerate the pure series solvents such as methyl alcohol, ethanol, n-propyl alcohol etc.The usage quantity of solvent is not particularly limited, but with respect to compound (10) 1g, is generally 1～100ml.
Temperature of reaction is the temperature range from room temperature to the solvent boiling point that uses.Reaction times is determined by reaction scale, but is generally several minutes～tens of hours.
C) alkali exists the lower aryl compound that makes formula (12) expression (below, be sometimes referred to as " compound (12) ") to react manufacturing objective compounds (7) with compound (11).(in the formula (12), X, n and Cy and above-mentioned same meaning, X ' expression fluorine atom etc.）
With respect to (11) 1 moles of compounds, the usage quantity of compound (12) is generally 1～2 mole, is preferably 1.0～1.2 moles.
As alkali, can enumerate the metal hydroxidess such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide; The metal alcoholates such as sodium methylate, sodium ethylate, potassium methylate, potassium ethylate, potassium tert.-butoxide; The metal hydrides such as sodium hydride, potassium hydride KH, hydrolith; Triethylamine, diisopropyl ethyl amine, pyridine, 1, the organic basess such as 8-diazabicyclo ［ 5.4.0 ］ 11 carbon-7-alkene (DBU), Isosorbide-5-Nitrae-diazabicyclo ［ 2.2.2 ］ octane.With respect to (11) 1 moles of compounds, the usage quantity of alkali is generally 1～2 mole.
This reaction is carried out in solvent.The solvent that uses is so long as to the solvent of reaction as inertia, just be not particularly limited.Can enumerate and as carrying out the same solvent of illustrative solvent phase for the manufacture of the solvent of compound (2).The usage quantity of solvent is not particularly limited, but with respect to compound (11) 1g, is generally 1～100ml.
Temperature of reaction is the temperature range from-20 ℃ to the solvent boiling point that uses.Reaction times is determined by reaction scale, but is generally several minutes～tens of hours.
In arbitrary reaction, all can react and carry out purifying by known habitual purification process such as common post-processing operation and distillation as required, recrystallize, column chromatographies, the segregation target compound after finishing.
The structure of target compound can be identified, confirm by known analysis means such as IR spectrum, NMR spectrum, mass spectrum, ultimate analyses.
(noxious organism control agent)
Aryloxy carbamide compound of the present invention or its salt (below be sometimes referred to as " the compounds of this invention ") are to be effective to preventing and kill off of harmful organism such as various insects (comprising the mite class) or phytopathogens.Especially be effective as miticide or sterilant.
(miticide)
Then, to describing with the miticide of the compounds of this invention as effective constituent.The compounds of this invention is owing to having extremely adult, kill nymph, kill the effects such as larva and ovicidal, thus can be used in prevent and kill off farm crop with the harmful organisms such as mite class.Especially for farm crop, fruit tree, flowers, trees with the preventive effect of mite class excellent.
The example that will become the mite class (Acari) of preventing and kill off object is shown in following.
(1) the flour mite class (Acaridida) of Astigmata (Astigmata):
(a) mite of Tyroglyphidae (Acaridae), for example the root mite belongs to thorn foot root mite (Rhizoglyphus echinopus), the anhui fritillary (Rhizoglyphus robini) of (Rhizoglyphus spp.); The tyrophagus putrescentiae (Tyrophagus putrescentiae) of Tyrophagus (Tyrophagus spp.), pawl food junket mite (Tyrophagus neiswanderi), dirt food junket mite (Tyrophagus perniciosus), seemingly eat junket mite (Tyrophagus similis); Other, Acarus siro (Acarus siro), oval baking soda mite (Aleuroglyphus ovatus), bacterium food are had a liking for bacterium mite (Mycetoglyphus fungivorus);
(2) the spoke mite class (Actinedida) of front valve suborder (Prostigmata)
(a) mite of Tetranychidae (Tetranychidae), for example Bryobia praetiosa (Bryobia praetiosa) of chrysanthemum Bryobia (Bryobia spp.), carex fruit mite (Bryobia rubrioculus); The north beginning tetranychid (Eotetranychus boreus) of Eotetranychus (Eotetranychus spp.) for example, knee shape beginning tetranychid (Eotetranychus geniculatus), Lee tetranychid (Eotetranychus pruni) that begins, crotch beginning tetranychid (Eotetranychus uncatus), evergreen chinquapin beginning tetranychid (Eotetranychus shii), mulberry beginning tetranychid (Eotetranychus suginamensis), Piao beginning tetranychid (Eotetranychus celtis), Eotetranychus smithi (Eotetranychus smithi), Asia beginning tetranychid (Eotetranychus asiaticus), tangerine beginning tetranychid (Eotetranychus kankitus); The mango unguiculus mite (Oligonychus mangiferus) of Oligonychus (Oligonychus spp.) for example, junket pears tetranychid (Oligonychus perseae), the smooth dragon spruce tetranychid (Oligonychus pustulosus) of shrimp, tamarack unguiculus mite (Oligonychus karamatus), cryptomeria unguiculus mite (Oligonychus hondoensis), ilex Oligonychus (Oligonychus ilicis), oligonychus ununguis (Oligonychus ununguis) Zhen Kaji unguiculus mite (Oligonychus shinkajii), sugarcane tetranychid (Oligonychus orthius); For example Panonychus citri belongs to citrus red mite (crm) (Panonychus citri), mulberry Panonychus citri (Panonychus mori), the panonychus ulmi (Panonychus ulmi) of (Panonychus spp.); The for example tetranychus viennensis (Tetranychus viennensis) of Tetranychus (Tetranychus spp.), water oak tetranychid (Tetranychus quercivorus), thorn apple tetranychid (Tetranychus ludeni), bean spider mite (Tetranychus phaselus), carmine spider mite (Tetranychus cinnabarinus), kamisawa tetranychus (Tetranychus kanzawai), T.urticae Koch (Tetranychus urticae); For example lack the scarce pawl mite (Aponychus firmianae) of SchizotetranychusnanjingensisMaetYuan (Aponychus corpuzae), Chinese parasol tree that the pawl mite belongs to (Aponychus spp.); For example the greenery mite (Sasanychus akitanus) of green Tetranychus (Sasanychus spp.), the green tetranychid of a Ji (Sasanychus pusillus); For example split Stephanitispyrioides (Shizotetranychus celarius), Chinese silvergrass Schizotetranychus (Shizotetranychus miscanthi), longue Schizotetranychus (Shizotetranychuslongus), former Schizotetranychus (Shizotetranychus schizopus), the Le Shi Schizotetranychus (Shizotetranychus recki) of pawl Tetranychus (Shizotetranychus spp.); Other, peacock Du Ke tetranychid (Tuckerella pavoniformis), Tetranychina harti (Tetranychina harti), Sapporo tetranychid (Yezonychus sapporensis);
(b) mite of Tenuipalpidae (Tenuipalpidae), for example the Liu Shi short hairs mite (Brevipalpus lewisi) of short whisker Acarapis (Brevipalpus spp.), Root and stem of Cholla short hairs mite (Brevipalpus russulus), priet mite (Brevipalpus obovatus), purplish red short hairs mite (Brevipalpus phoenicis); The for example Pacific Ocean false spider mite (Tenuipalpus pacificus) of Tenuipalpus (Tenuipalpus spp.), persimmon false spider mite (Tenuipalpus zhizhilashviliae); Other, the pineapple mite (Dolichotetranychus floridanus) that comes into leaves;
(c) mite of Eriophyidae (Eriophyidae), for example the persimmon goitre mite (Aceria diospyri) of Genus Aceria (Aceria spp.), banyan goitre mite (Aceria ficus), Japanese aceria (Aceria japonica), matrimony vine goitre mite (Aceria kuko), China pink bud aceria (Aceria paradianthi), matrimony vine leaf mining goitre mite (Aceria tiyingi), turmeric goitre mite (Aceria tulipae), jielu grass mite (Aceria zoysiea); For example pseudo-pears rust tick (Eriophyes chibaensis), the plum of Eriophyes (Eriophyes spp.) are saved mite (Eriophyes emarginatae); The for example Aculops lycopersici (Aculops lycopersici) of peronium Eriophyes (Aculops spp.), tangerine peronium goitre mite (Aculops pelekassi); The for example Aculus fockeui (Aculus fockeui) of Aculus (Aculus spp.), thorn apple rust mite (Aculus schlechtendali); Other, grape lacks goitre mite (Epitrimerus pyri) on joint goitre mite (Colomerus vitis), grape leaf rust mite (Calepitrimerus vitis), Ryukyu tangerine rust mite (Phyllocotruta citri), the secondary beautiful goitre mite (Paracalacarus podocarpi) of Podocarpus macrophyllus, tealeaves goitre mite (Calacarus carinatus), tea point leaf goitre mite (Acaphylla theavagrans), Folium chrysanthemi aceria (Paraphytoptus kikus), the pears;
(d) mite of Tarsonemidae (Tarsonemidae), for example the double leaf tarsonemid mite (Tarsonemus bilobatus) of Tarsonemus (Tarsonemus spp.), Webster tarsonemid mite (Tarsonemus waitei); Other, primrose herbivore mite (Phytonemus pallidus), Polyphagotarsonemus latus Banks (Polyphagotarsonemus latus);
(e) mite of leaf pawl mite section (Penthaleidae), for example leaf pawl mite belongs to Chinese cabbage mite (Penthaleus erythrocephalus), the wheat leaf pawl mite (Penthaleus major) of (Penthaleus spp.);
And, excellent to the preventive effect of the mite class that parasitizes animal.The mite class that parasitizes animal comprises: parasitize the back of the body, oxter, abdomen of the animal (host animal) as the host, interior thigh section etc. and obtain the nutrition sources such as blood, scurf and the mite class of surviving from animal, and fly to the back of the body, buttocks etc. of host animal and obtain the nutrition sources such as blood, scurf and the mite class of surviving from animal.As the host animal that becomes object, can enumerate dog, cat, mouse, rat, hamster, cavy, squirrel, rabbit, weasel; Pet bird (for example pigeon, parrot, starling bird, mannikin, parrot, Root of seven-sisters Japanese Rose bird, canary bird); Ox, horse, pig, sheep, goat; Poultry (for example duck, chicken, quail, goose); Honeybee (such as apis mellifera, Japanese honeybee) etc.
The example that will become the mite class (Acari) of preventing and kill off object is shown in following.
(1) the mite class (mite) of Mesostigmata (Mesostigmata)
(a) mite of Dermanyssidae (Dermanyssidae), for example Dermanyssus gallinae (Dermanyssus gallinae);
(b) mite of opposing needling mite section (Macronyssidae), for example northern fowl mite (Ornithonyssus sylviarum) of Ornithonyssus (Ornithonyssus spp.), capsule fowl thorn mite (Ornithonyssus bursa), ornithonyssus bacoti (Ornithonyssus bacoti);
(c) mite of Laelapidae (Laelapidae), for example laelaps echidninus (Laelaps echidninus) of Laelaps (Laelaps spp.), Laelaps jettmari (Laelaps jettmari); Mites (Tropilaelaps clarae)
(d) mite of watt mite section (Varroidae), for example the Di Siwa mite (Varroa destructor) of Varroa (Varroa spp.), Varroa jacobsoni (Varroa jacobsoni), engler watt mite (Varroa underwoodi);
(2) the true tick class (tick) of valve order (Metastigmata) after
(a) Argasidae (Argasidae) mite, for example adobe tick (Argas persicus) of Argas (Argas spp.), argas reflexus (Argas reflexus); The carapatos (Ornithodoros moubata) of Ornithodoros (Ornithodoros spp.) for example;
(b) mite of hard tick section (Ixodidae), for example haemaphysalis conicinna (Haemaphysalis concinna) of Haemaphysalis (Haemaphysalis spp.), Haemaphysalis punctata (Haemaphysalis punctata), cinnabar blood tick (Haemaphysalis cinnabarina), mouse ear blood tick (Haemaphysalis otophila), haemaphysalis leachi (Haemaphysalis leachi), haemaphysalis longicornis (Haemaphysalis longicornis), haemaphysalis mageshimaensis (Haemaphysalis mageshimaensis), haemaphysalis yeni (Haemaphysalis yeni), haemaphysalis campanulata (Haemaphysalis campanulata), black rabbit blood tick (Haemaphysalis pentalagi), haemaphysalis flava (Haemaphysalis flava), huge sour jujube blood tick (Haemaphysalis megaspinosa), Haemaphysalis japonica (Haemaphysalis japonica), Dao Shi blood tick (Haemaphysalis douglasi); For example the lone star tick (Amblyomma americanum) of Amblyomma (Amblyomma spp.), illuminated flower tick (Amblyomma variegatum), Bont (Amblyomma maculatum), Hebrew spend tick (Amblyomma hebraeum), card to prolong colored tick (Amblyomma cajennense), tortoise-shell shaped flower tick (Amblyomma testudinarium); For example hard tick belongs to the castor bean tick (Ixodes ricinus) of (Ixodes spp.), the hard tick of hexagonal (Ixodes hexagonus), ixodes canisuga (Ixodes canisuga), ixodes pilosus (Ixodes pilosus), ixodes rubicundus (Ixodes rubicundus), the hard tick of scapulet (Ixodes scapularis), ixodes holocyclus (Ixodes holocyclus), ixodes ovatus (Ixodes ovatus), ixodes persulcatus (Ixodes persulcatus), Ixodes japonensis (Ixodes nipponensis); Boophilus microplus (Rhipicephalus(Boophilus) microplus of ox tick subgenus (Boophilus spp.) for example), decolouring (ox tick) fan head tick (Rhipicephalus(Boophilus) decoloratus), tool ring (ox tick) fan head tick (Rhipicephalus(Boophilus) annulatus), square (ox tick) fan head tick (Rhipicephalus(Boophilus) calceratus is arranged); The rhipicephalus evertsi (Rhipicephalus evertsi) of Rh (Rhipicephalus spp.) for example, brown dog tick (Rhipicephalus sanguineus), rhinpicephalus bursa (Rhipicephalus bursa), Rhipicephalus appendicularis (Rhipicephalus appendiculatus), rhinpicephalus capensis (Rhipicephalus capensis), R.turanicus (Rhipicephalus turanicus), praise than western fan head tick (Rhipicephalus zambeziensis); For example the dermacentor marginatus (Dermacentor marginatus) of Dermacentor (Dermacentor spp.), dermacentor reticulatus (Dermacentor reticulatus), decorative pattern are removed from office tick (Dermacentor pictus), winter tick (Dermacentor albipictus), Dermacentor andersoni (Dermacentor andersoni), Dermacentor variabilis (Dermacentor variabilis);
(3) the flour mite class (Acaridida) of Astigmata (Astigmata)
(a) mite of itch mite section (Psoroptidae), for example psoroptes communis (Psoroptes ovis) of Psoroptes (Psoroptes spp.), psoroptes cuniculi (Psoroptes cuniculi), psoroptes equi (Psoroptes equi); For example sufficient mite belongs to the ox foot mite (Chorioptes bovis) of (Chorioptes spp.); The dog ear mite (Otodectes cynotis) of Notoedres (Otodectes spp.);
(b) mite of Sarcoptidae (Sarcoptidae), for example itch mite belong to (Sarcoptes spp.) Sarcoptes scabiei hominis (Sarcoptes scabiei), sarcoptes canis (Sarcoptes canis), Sarcoptes bovis (Sarcoptes bovis), Sarcoptes ovis (Sarcoptes ovis), chamois itch mite (Sarcoptes rupicaprae),
Sarcoptes equi (Sarcoptes equi), Sarcoptes suis (Sarcoptes suis); For example carry on the back anus and belong to (Notoedres spp.), cat back of the body anus mite (Notoedres cati);
(c) mite of knee mite section (Knemidokoptidae), for example knee belongs to the sudden change knee mite (Knemidokoptes mutans) of (Knemidokoptes spp.);
(4) the spoke mite class (Actinedida) of Prostigmata (Prostigmata)
(a) mite of Demodicidae (Demodixidae), for example demodicidosis (Demodex canis) of Demodex (Demodex spp.), ox demodicid mite (Demodex bovis), sheep demodicid mite (Demodex ovis), Demodex caprae (Demodex caprae), horse demodicid mite (Demodex equi), the sharp demodicid mite (Demodex caballi) of kappa, pig demodicid mite (Demodex suis), cat demodicid mite (Demodex cati);
(b) mite of Trombidiidae (Trombiculidae), for example eutrombicula alfreddugesi (Trombicula alfreddugesi) of Trombidium (Trombicula spp.), bete rouge (Trombicula akamushi);
(c) mite of Tarsonemidae (Tarsonemidae), for example honeybee shield mite belongs to the Wu Shi honeybee shield mite (Acarapis woodi) of (Acarapis spp.);
(sterilant)
And, the compounds of this invention can be used for farm crop with the mite class beyond the preventing and kill off of the harmful organisms such as insect, sanitary insect pest, pest of stored grain, clothing insect, house insect.
To become prevent and kill off object example be shown in following.
(1) lepidoptera pest, for example prodenia litura (Spodoptera litura), lopper worm (Mamestra brassicae), black cutworm (Agrotis ypsilon), beans three-spotted phytometra (Autographa nigrisigna), small cabbage moth (Plutella xylostella), tea olethreutid (Adoxophyes honmai), rear yellow leaf curl moth (Homona magnanima), peach moth fruit (Carposina sasakii), oriental fruit months (Grapholitha molesta), citrus leaf-miner (Phyllocnistis citrella), the thin moth of tea (Caloptilia theivora), the little thin moth (Phyllonorycter ringoniella) of diving of Jin Wen, gypsymoth (Lymantria dispar), Euproctis pseudoconspersa (Euproctis pseudoconspersa), striped rice borer (Chilo suppressalis), Cnaphalocrocis medinali(rice leaf roller) (Cnaphalocrocis medinalis), Pyrausta nubilalis (Hubern). (Ostrinia nubilalis), fall webworms (Hyphantria cunea), Cadra cautella (Cadra cautella), Heliothis (Heliothis spp.), Helicoverpa (Helicoverpa), ground Noctua (Agrotis spp.), casemaking clothes moth (Tinea translucens), carpocapsa pononella (Cydia pomonella), pink bollworm (Pectinophora gossypiella) etc.;
(2) Hemiptera insect, for example black peach aphid (Myzus persicae), cotten aphid (Aphis gossypii), radish aphid (Lipaphis erysimi), rhopalosiphum padi (Rhopalosiphum padi), point honeybee edge stinkbug (Riptortus clavatus), intend green stinkbug (Acrosternum hilare), arrowhead scales (Unaspis yanonensis), Kang Shi mealybug (Pseudococcus comstocki), greenhouse whitefly (Trialeurodes vaporariorum), Bemisia tabaci (Bemisia tabaci), Bemisia argentifolii (Bemisia argentifolii), pear sucker (Psylla pyrisuga), pear lace bug (Stephanitis nashi), brown paddy plant hopper (Nilaparuata lugens), small brown rice planthopper (Laodelphax stratella), white backed planthopper (Sogatella furcifera), rice green leafhopper (Nephotettix cincticeps) etc.;
(3) beetle order insect, for example Phyllotreta striolata (Phyllotreta striolata), purree cucumber beetle (Aulacophora indica), colorado potato bug (Leptinotarsa decemlineata), rice water weevil (Lissorhoptrus oryzophilus), rice weevil (Sitophilus oryzae), Callosobruchus chinensis (Callosobruchus chinensis), Japanese beetle (Popillia japonica), red metal rutelian (Anomala rufocuprea), chrysomelid genus (Diabrotica spp.), lasioderma serricorne (Lasioderma serricorne), Lyctus brunneus Stephens (Lyctus brunneus), Monochamus alternatus (Monochamus alternatus), hickie longicorn beetle (Anoplophora malasiaca), click beetle belongs to (Agriotes spp.), the 28 stars worm (Epilachna vigintioctopunctata) of wafing, grain peat (Tenebroides mauritanicus), anthonomus grandis (Anthonomus grandis) etc.;
(4) Diptera pest, such as melon trypetid (Bactrocera cucurbitae), citrus fruit fly (Bactrocera dorsalis), kind fly (Delia platura), Hydrellia griseola (Hydrellia griseola), drosophila melanogaster (Drosophila melanogaster) etc.;
(5) Thysanoptera insect, such as palm thrips (Thrips palmi), tea golden thistle horse (Scirtothrips dorsalis) etc.;
(6) Hymenoptera insect, such as monomorium pharaonis (Monomorium pharaonis), yellow sparrow honeybee (Vespa simillima), yellow-winged cabbage sawfly (Athalia rosae) etc.;
(7) orthoptera pest is such as Asiatic migrotory locust (Locusta migratoria) etc.;
(8) Blattodea (Blattodea) insect, such as Groton bug (Blattella germanica), Peroplaneta fluligginosa (Periplaneta fuligginosa), the large Lian (Periplaneta japonica) of Japan, periplaneta americana (Periplaneta americana), Australian cockroach (Periplaneta australasiae) etc.;
(9) Isoptera insect, such as Coptotermes formosanus Shtrari． (Coptotermes formosanus), eastern subterranean termite (Reticulitermes speratus) etc.,
(10) plant parasitic nematodes class, such as root knot nematode (Meloidogyne incognita), pratylenchus class, soybean cyst nematode Heterodera glycines (Heterodera glycines), leaf bud nematode (Aphelenchoides besseyi), pine wood nematode (Bursaphelenchus xylophilus) etc.;
(exterior parasite agent)
And the compounds of this invention is excellent to the preventive effect of the epizoon beyond the mite class that parasitizes animal.
The example that will become the Phthiraptera class (Phthiraptera) of agent for preventing and eliminating object is shown in following.
(1) the lice class (louse) of lice suborder (Anoplura)
(a) lice of haematopinidae (Haematopinidae), for example haematopinus asina (Haematopinus asini) of Haematopinus (Haematopinus spp.), haematopinus eurysternus (Haematopinus eurysternus), haematopinus suis (Haematopinus suis);
(b) lice of Lernaeopodidae (Linognathidae), for example the sour jujube jaw lice (Linognathus setosus) of Linognathus (Linognathus spp.), Linognathus vituli (Linognathus vituli), sheep jaw lice (Linognathus ovillus), avette jaw lice (Linognathus oviformis), sheep foot jaw lice (Linognathus pedalis), leptoprosopy jaw lice (Linognathus stenopsis); For example blind lice belongs to the solenoptes capillatus (Solenopotes capillatus) of (Solenopotes spp.);
(2) Amblycera (Amblycera) nibbles a mao lice class (biting louse)
(a) Menoponidae (Menoponidae) nibble a mao lice, for example the chick poultry louse (Menacanthus stramineus) of Menacanthus (Menacanthus spp.), angle chicken lice (Menacanthus cornutus), pale chicken lice (Menacanthus pallidulus) are arranged; For example the chicken lice belongs to the shaft louse (Menopon gallinae) of (Menopon spp.);
(3) Ischnocera (Ischnocera) nibbles a mao lice class (biting louse)
(a) Philopteridae (Philopteridae) nibbles a mao lice, for example columbicola columbae (Columbicola columbae) of Columbicola (Columbicola spp.); The cuclotogaster heterographus (Cuclotogaster heterographus) of Cuclotogaster (Cuclotogaster spp.) for example; For example the irregular corners poultry louse (Goniodes dissimilis) of Goniodes (Goniodes spp.), big angle poultry louse (Goniodes gigas), chicken are justified poultry louse (Goniodes gallinae); The oval lice of chicken (Lipeurus caponis) of long Trichodectes (Lipeurus spp.) for example;
(b) Trichodectidae (Trichodectidae) nibble a mao lice, for example the ox louse (Bovicola bovis) of Bovicola (Bovicola spp.), sheep lice (Bovicola ovis), tool limit hair lice (Bovicola limbata), goat lice (Bovicola caprae), horse sting lice (Bovicola equi); The Trichodectes latus (Trichodectes canis) of Trichodectes (Trichodectes spp.) for example; The cat lice (Felicola subrostrata) of Felicola (Felicola spp.) for example;
Be shown in the example of flea class (Siphonaptera) following.
(a) flea of Tungidae (Tungidae), for example chigo (Tunga penetrans) of Dermatophilus (Tunga spp.);
(b) flea of Pulicidae (Pulicidae), for example ctenocephalides canis (Ctenocephalides canis) of Ctenocephalus (Ctenocephalides spp.), ctenocephalides felis (Ctenocephalides felis); The hedgehog flea (Archaeopsylla erinacei) of Archaeopsylla (Archaeopsylla spp.) for example; For example objective flea belongs to the Xanthopsyllacheopis (Xenopsylla cheopis) of (Xenopsylla spp.); For example flea belongs to the Pulex irritans (Pulex irritans) of (Pulex spp.); The echidnophaga gallinacea (Echidnophaga gallinacea) of Echidnophaga (Echidnophaga spp.) for example;
(c) flea of Ceratophyllidae (Ceratophyllidae), for example ceratophyllus gallinae (Ceratophyllus gallinae) of Ceratophyllus (Ceratophyllus spp.), ceratophyllus anisus (Ceratophyllus anisus); The ceratophyllus fasciatus (Nosopsyllus fasciatus) of Nosopsyllus (Nosopsyllus spp.) for example;
(d) flea of Leptopsyllidae (Leptopsyllidae), for example leptopsylla musculi (Leptopsylla segnis) of Ctenopsyllus (Leptopsylla spp.);
As other the epizoon that becomes object, also can enumerate the insect of Hemiptera.
Be shown in the example of Hemiptera (Hemiptera) following.
(a) insect of Cimicidae (Cimicidae), for example bed bug (Cimex lectularius) of Cimex (Cimex spp.);
(b) for example Triatoma of the insect of Reduviidae (Reduviidae), and then Triatominae (Triatominae) (Panstrongylus spp.); The phodnius prolixus (Rhodnius prolixus) of Rhodnius (Rhodnius spp.) for example; The unchuca (Triatoma infestans) of Triatoma (Triatoma spp.) for example;
It also is effective belonging to Diptera (Diptera) insect of stinging stinging property insect (maggot of chewiness fly, the adult fly of sucking blood, the dipteral larva of movability, tachinid) for other.
Be shown in the example of Diptera class (Diptera) following.
(1) Nemocera (Nematocera)
(a) mosquito of Dulicidae (Culicidae), for example culex pipiens fatigans (Culex quinquefasciatus) of Culex (Culex spp.), culex pipiens pollens (Culex pipiens pallens), culex tarsalis (Culex tarsalis), Culex molestus (Culex pipiens molestus), Culex quinquefasciatus (Culex pipiens fatigans), three spot man mosquitos (Culex tritaeniorhynchus summorosus); The armigeres obturbans (Armigeres subalbatus) of Armigeres (Armigeres spp.) for example; The for example anopheles costalis (Anopheles gambiae) of Anopheles (Anopheles spp.), anopheles maculipennis (Anopheles maculipennis), Anopheles sinensis (Anopheles sinensis), Anopheles lesteri (Anopheles lesteri); The for example Aedes aegypti (Aedes aegypti) of Aedes (Aedes spp.), Aedes albopictus (Aedes albopictus), aedes taeniorhynchus (Aedes taeniorhynchus), aedes togoi (Aedes togoi), Japanese Aedes vexans (Aedes vexans nipponii);
(b) Simulium reptans (Simulium reptans) of the buffalo gnat of Simulidae (Simuliidae), for example Simulium (Simulium spp.), decorations buffalo gnat (Simulium ornatum), charming buffalo gnat (Simulium venustum), horse buffalo gnat (Simulium salopiense); The large buffalo gnat of yellow pin (Prosimulium yezoense) of Prosimulium (Prosimulium spp) for example;
(c) midge of Heleidae (Ceratopogonidae), for example storehouse, the waste river midge (Culicoides arakawae) of Bitting midge (Culicodes spp.), storehouse, edge midge (Culicoides pictimargo), your boathouse midge (Culicoides kibunensis), consubstantiality storehouse midge (Culicoides homotomus), culicoides oxystoma (Culicoides oxystoma), Japan storehouse midge (Culicoides nipponensis), C.punctatus (Culicoides punctatus), clouding storehouse midge (Culicoides maculatus), Ming Bianku midge (Culicoides matsuzawai)
(2) Brachycera
(a) horsefly of Tabanidae (Tabanidae), for example Gadfly (Tabanus spp.) noisy disturb horsefly (Tabanus bromius), Si Botebu iron like that (Tabanus spodopterus), tabanus atratus (Tabanus atratus), gadbee (Tabanus sudeticus), triangle horsefly (Tabanus trigonus), ox horsefly (Tabanus chrysurus), triple horsefly (Tabanus trigeminus), yellow bar horsefly (Tabanus fulvimedioides), she gives horsefly (Tabanus iyoensis); For example the black tail spot horsefly (Chrysops caecutiens) of Chrysops (Chrysops spp.), abandon spot horsefly (Chrysops relictus), dense patch horsefly (Chrysops suavis), chrysops japonicus (Chrysops japonicus);
(e) fly of Nuscidae (Muscidae), for example housefly (Musca domestica), the north of Muscina (Muscina spp.) dwell housefly (Musca bezzii), musca hervei (Musca hervei), musca conducens (Musca conducens), false stable fly (Musca stabulans); The tatukira (Stomoxys calcitrans) of Genus Stomoxys (Stomoxys spp.) for example; The for example Haematobia irritans (Haematobia irritans) of Haematobia (Haematobia spp.), east horn fly (Haematobia irritans exigua), ox blood fly (Haematobia stimulans); The Fannia canicularis (Fannia canisularis) of Fannia (Fannia spp.);
(c) Glossina of Glossinidae (Glossinidae) (Glossina spp.);
(e) fly of Hippoboscidae (Hippoboscidae), for example ked (Melophagus ovinus) of Melophagus (Melophagus spp.);
(e) fly of Calliphoridae (Calliphoridae), for example roomy calliphorid of Calliphora (Calliphora) (Calliphora lata); Lucilia cuprina (Lucilia(Phaenicia) cuprina of Lucilia (Lucilia spp.) for example), lucilia sericata (Lucilia(Phaenicia) sericata), Lucilia illustris (Lucilia illustris); The for example cochliomyia bominovorax of Carysomyia (Chrysomyia.spp.) (Chrysomya hominivorax), the naked golden fly of hoary hair (Chrysomya chloropyga), maggot disease gold fly (Chrysomya bezziana);
(f) fly of Destridae (Oestridae), for example Cuterebra of yellow fly subfamily (Cuterebrinae) (Cuterebra spp.); For example torsalo subfamily (Hypodermatinae) and bomb fly (Hypoderma bovis) Hypoderma (Hypoderma spp.), heel fly (Hypoderma lineatum); For example gasterophilus leach (Gasterophilinae) and Gasterophilus intestinalis (Gasterophilus intestinalis) Gasterophilus (Gasterophilus spp.), Gasterophilus haemorrhoidalis (Gasterophilus haemorroidalis), microgastria fly (Gasterophilus inermis), gasterophilus nasalis (Gasterophilus nasalis), black angle stomach fly (Gasterophilus nigricornis), gastrophilus pecorum (Gasterophilus pecorum); Botfly subfamily (Oestrinae) and Oestrus ovis (Oestrus ovis) Oestrus (Oestrus spp.) for example;
(sterilant)
Then, the sterilant take the compounds of this invention as effective constituent is described.The compounds of this invention is owing to having excellent germicidal action, therefore can be used for preventing and kill off the thread fungus of broad variety, for example from the Plant diseases of the bacterium that belongs to oomycetes (Oomycetes), sac fungi (Ascomycetes), imperfect fungi (Deuteromycetes), club fungi (Basidiomycetes).
The example that will become the Plant diseases of preventing and kill off object is shown in following.
" beet ": brown spot (Cercospora beticola), black root (Aphanomyces cochlloides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris) etc.
" peanut ": brown spot (Mycosphaerella arachidis), black spot (Mycosphaerella berkeleyi) etc.
" cucumber ": Powdery Mildew (Sphaerotheca fuliginea), oidium (Pseudoperonospora cubensis), climing rot (Mycosphaerella melonis), dead arm (Fusarium oxysporum), sclerotium disease (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), anthrax (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassicola), seedling blight (Pythium debaryanam, Rhizoctonia solani Kuhn), bacterial leaf spot (Pseudomonas syringae pv.Lecrymans) etc.
" tomato ": gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans) etc.
" eggplant ": gray mold (Botrytis cinerea), Black Rotten (Corynespora melongenae), Powdery Mildew (Erysiphe cichoracearum), suede bacterial plaque sick (Mycovellosiella nattrassii) etc.
" strawberry ": gray mold (Botrytis cinerea), Powdery Mildew (Sohaerotheca humuli), anthrax (Colletotrichum acutatum, Colletotrichum fragariae), Phytophthora cactorum sick (Phytophthora cactorum) etc.
" onion ": neck rot (Botrytis allii), gray mold (Botrytis cinerea), hickie leaf blight (Botrytis squamosa), oidium (Peronospora destructor)
" Caulis et Folium Brassicae capitatae ": anbury (Plasmodiophora brassicae), soft rot (Erwinia carotovora), oidium (Peronospora parasitica) etc.
" French beans ": sclerotium disease (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea) etc.
" apple ": Powdery Mildew (Podosphaera leucotricha), black spot (Venturia inaequalis), blossom rot (Monilinia mali), diplostomiasis (Mycosphaerella pomi), canker (Valsa mali), spot defoliation (Alternaria mali), red-star like disease (Gymnosporangium yamadae), ring spot (Botryosphaeria berengeriana), anthrax (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), fly pinta (Zygophiala jamaicensis), sooty mold (Gloeodes pomigena) etc.
" persimmon ": Powdery Mildew (Phyllactinia kakicola), anthrax (Gloeosporium kaki), angle spot defoliation disease (Cercospora kaki) etc.
" peach ": brown heart (Monilinia fructicola), black spot (Cladosporium carpophilum), Phomopsis sick (Phomopsis sp.) etc.
" cherry ": brown heart (Monilinia fructicola) etc.
" grape ": gray mold (Botrytis cinerea), Powdery Mildew (Uncinula necator), late blight (Glomerella cingulata, Colletotrichum acutatum), oidium (Plasmopara viticola), anthrachose of grape (Elsinoe ampelina), brown spot (Pseudocercospora vitis), Black Rotten (Guignardia bidwellii) etc.
" pears ": black spot (Venturia nashicola), red-star like disease (Gymnosporangium asiaticum), black spot (Alternaria kikuchiana), ring spot (Botryosphaeria berengeriana), Powdery Mildew (Phyllactinia mali) etc.
" tea ": zonate spot (Pestalotia theae), anthrax (Colletotrichum theae-sinensis) etc.
" citrus ": shot hole (Elsinoe fawcetti), penicilliosis (Penicillium italicum), green mould (Penicillium digitatum), gray mold (Botrytis cinerea), diplostomiasis (Diaporthe citri), Peptic Ulcers (Xanthomonas campestris pv.Citri) etc.
" wheat ": Powdery Mildew (Erysiphe graminis f.sp.tritici), head blight (Gibberella zeae), leaf rust (Puccinia recondita), brown snow maize ear rot (Pythium iwayamai), snow red rot (Monographella nivalis), wheat-based maize ear rot (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), glume blight (Leptosphaeria nodorum), avenge rotten sclerotium oryzicola (Typhula incarnata), snow big grain sclerotinia rot (Myriosclerotinia borealis), damping-off (Gaeumanomyces graminis) etc.
" barley ": stripe disease (Pyrenophora graminea), clouding sick (Rhynchosporium secalis), smut (Ustilago tritici, U.nuda) etc.
" rice ": rice blast (Pyricularia oryzae), banded sclerotial blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), Folium Sesami pinta (Cochliobolus miyabeanus), the rotten mildew (Pythium graminicola) of dogstail, bacterial leaf-blight (Xanthomonas oryzae), bacillary seedling blight (Burkholderia plantarii), brown streak (Acidovorax avenae), the withered bacterial disease of paddy (Burkholderia glumae)
" tobacco ": sclerotium disease (Sclerotinia sclerotiorum), Powdery Mildew (Erysiphe cichoracearum) etc.
" turmeric ": gray mold (Botrytis cinerea) etc.
" Western jielu grass ": snow big grain sclerotinia rot (Sclerotinia borealis), samping off (Pythium aphanidermatum) etc.
" orchard grass ": Powdery Mildew (Erysiphe graminis) etc.
" soybean ": anaphylactoid purpura (Cercospora kikuchii), oidium (Peronospora Manshurica), cane blight (Phytophthora sojae) etc.
" potato ": late blight (Phytophthora infestans) etc.
The compounds of this invention is that poisoning is few, low to the toxicity of fish, warm-blooded animal, safe compound particularly.
Noxious organism control agent of the present invention contains be selected from the compounds of this invention at least a kind as effective constituent.
In addition, noxious organism control agent of the present invention can only contain the compounds of this invention, also can contain the carriers such as solid carrier, liquid vehicle, gas shape carrier.In addition, noxious organism control agent of the present invention can be impregnated in the compounds of this invention in the base materials such as porous ceramic plate, non-woven fabrics.And, can also add as required tensio-active agent, other auxiliary.
But noxious organism control agent preparation of the present invention changes into the form that general agricultural chemicals can be taked, be wettable powder, granule, pulvis, emulsion, soluble powder, suspension agent, water dispersible granules, flowing agent, micro-capsule, aerosol, smoke substance, add hot flashing agent, smoking agent, in acaricidal situation, but preparation changes into the forms such as bait formulation.
As the additive that when making solid dosage, uses and carrier, can enumerate the vegetalitas powder such as soyflour, wheat-flour, the mineral micro mists such as diatomite, phosphatic rock, gypsum, talcum powder, wilkinite, agalmatolite, clay, organic and mineral compound such as Sodium Benzoate, urea, saltcake etc.
As the solvent that when making liquid dosage form, uses, can enumerate kerosene, dimethylbenzene and petroleum aromatic hydrocarbon, hexanaphthene, pimelinketone, dimethyl formamide, dimethyl sulfoxide (DMSO), alcohol, acetone, trichloroethane, methyl iso-butyl ketone (MIBK), mineral oil, vegetables oil, water etc.
The gas shape carrier that uses when making propellant can be enumerated butane gas, LPG, dimethyl ether, carbonic acid gas etc.
As the base material of poison bait, can enumerate the bait compositions such as grain flour, vegetables oil, sugar, crystalline cellulose; Butylated hydroxytoluene, the antioxidants such as dihydro guaiac acid fall; The sanitass such as dehydroacetic acid (DHA); Capsicum powder etc. prevents the preventing agent of eating by mistake that children or pet eat by mistake; The insect epigamic spices such as cheese spices, onion spice.
Preparation can add tensio-active agent as required in order to obtain even and stable form.As addible tensio-active agent, be not particularly limited.The polyoxyethylated alkyl phenyl ether of for example can having enumerated addition, addition polyoxyethylated alkyl oxide, addition polyoxyethylated high-grade aliphatic ester, addition polyoxyethylated sorbitan high-grade aliphatic ester, addition the nonionic surface active agent such as polyoxyethylated triphenylethylene base phenyl ether, addition the sulfuric acid of polyoxyethylated alkyl phenyl ether, alkylbenzene sulfonate, the sulfuric acid of higher alcohols, sulfonated alkyl naphathalene, polycarboxylic acid's salt, sulfonated lignin, the formaldehyde condensation products of sulfonated alkyl naphathalene, the multipolymer of iso-butylene-maleic anhydride etc.
For the content of the compounds of this invention in the preparation, usually be preferably 0.01～90 % by weight with respect to preparation integral body, more preferably 0.05～85 % by weight.
The wettable powder of gained, emulsion, flowing agent, soluble powder, water dispersible granules are diluted with water to normality like this, intersperse among plant or soil after making solution, suspension or emulsion, in addition, pulvis, granule can directly intersperse among plant or soil.
In addition, when using miticide as epidemic prevention, can directly use the preparation that provides with forms such as finish, aerosol, smoke substance, poison bait, anti-mite sheets.
In addition, prevent and kill off when using miticide in the mite class of noxious organism control agent of the present invention being made the animal of the pets such as livestocks such as parasitizing ox, pig, dog, cat, with respect to host animal 1kg, can use the compounds of this invention with the amount of 0.01～1000mg ratio.
Prevent and kill off with miticide and can use by known veterinary method.As its method, for example when suppressing (systemic control) as purpose take general, can enumerate by tablet, capsule, steeping fluid, sneak into feed, suppository, injection (intramuscular, subcutaneous, intravenously, intraperitoneal etc.) etc. to the method for animals administer; When suppressing (non-systemic control) as purpose take non-general, can enumerate oiliness or aqueous liquid preparation through spraying, perfusion (pour-on), instil (spot on) etc. and the method for administration, in resin, mix miticide, should be shaped to the suitably shape such as necklace, ear tag by mixing thing, with its method of wearing to animal.
Noxious organism control agent of the present invention can be used with or and use with sterilant, other insecticidal/acaricidal agent, nematocides, extremely soil pests agent, plant modifying agent, synergistic agent, fertilizer, soil improvement agent, animal feed etc.
Can mix with noxious organism control agent of the present invention sterilant, other insecticidal/acaricidal agent, the nematocides that uses, the typical example that kills soil pests agent, plant modifying agent is shown in following.
Insecticidal/acaricidal agent, nematocides, extremely soil pests agent:
(1) organic (sulfo-) is phosphate-based: acephate, methyl pyrrole
Figure GDA00003484046400411
Phosphorus, parathion-methyl, ethyl parathion, bromophos_ethyl, the fragrant phosphorus of bromine, BRP, Chlorpyrifos 94, chlorpyrifos_methyl, the ethyl Chlorpyrifos 94, Zaprawa enolofos, cadusafos, carbophenothion, chlorethoxyfos, chlormephos, coumaphos oxygen analog, S-4087, cynock, CYAP, diazinon, SD-1750, Carbicron, Rogor, thiodemeton, demeton_S_methyl, dimethylvinphos, demeton_S_methyl, torak, diazinon, dichlofenthion, dioxabenzofos, thiodemeton, Nialate, ethoprop, etrimfos, EPN, fenamiphos, fenitrothion 95, Tiguvon, fensulfothion, pyrrole fluorine sulphur phosphorus, Dyfonate, good fortune wood pine; fosmethilan; Fei Dasong; isazofos; iodfenphos TOP; isofenphos;
Figure GDA00003484046400412
Azoles phosphorus, iprobenfos, the Malathion, Phosdrin, acephatemet, methidathion, monocrotophos, mecarbam, methacrifos, it is the power pine, omethoate, parathion-methyl, paraoxon, thiophos, parathion-methyl, Tsidial, Phosalone, R-1504, phosphamidon, phorate, Volaton, the methyl pirimiphosmethyl, pirimiphos ethyl, Profenofos, Toyodan, lythidathion, phosphorus worm prestige, Kayaphos, Propetamphos, Fac, pyridaphenthione, pyraclofos, Kui sulphur phosphorus, dioxabenzofos, sulprofos, dithione, tetrachlorvinphos, terbufos, triazophos, Trichlorphon, butyl pyrimidine phosphorus, Temephos, thiometon, vamidothion;
(2) carbamate system: alanycarb, aldicarb,
Figure GDA00003484046400421
Worm prestige, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, fenothiocarb, methiocarb, methomyl, oxamyl, Aphox, Propoxur, thiodicarb, triaxamate, ethiofencarb, fenobucarb, MIPC, MPMC, MTMC, pyridaphenthione, furathiocarb, XMC, aldoxycarb, allyxycarb, aminocarb,
Figure GDA00003484046400422
Worm prestige, bufencarb, the fear of poultry worm, butocarboxim, butanone sulfone prestige, worm prestige, dimetilan, formetanate, Ro 7-5050, metamsodium, meta-tolyl-N-methylcarbamate (MTMC), promecarb, thiofanox, trimethacarb, xylylcarb;
(3) pyrethroid system: allethrin, bifenthrin, cyfloxylate, β-cyfloxylate, cyhalothrin, high lambda-cyhalothrin, cyphenothrin, Cypermethrin, alphacypermethrin, Cypermethrin, the Z-Cypermethrin, Deltamethrin, the S-fenvalerate, ether chrysanthemum ester, Fenvalerate, fenvalerate, Imiprothrin, permethrin, prallethrin, pyrethrin, pyrethrin I, the pyrethrin II, card furan chrysanthemum ester, salifluofen, taufluvalinate, tefluthrin, Tetramethrin, tralomethrin, transfluthrin, the third Flumethrin, dimefluthrin, acrinathrin, cycloprothrin, halfenprox, flucythrinate, bioallethrin, benzyl furan alkene chrysanthemum ester, Permethrin, card furan chrysanthemum ester, trans permethrin, benefit is rather kept away, sweet smell is the Lamine not, fenpirithrin, brofluthrinate, trifluoro chrysanthemum ester, flumethrin, methoxy Bian Flumethrin, phenothrin, propyl benzene hydrocarbon chrysanthemum ester, Pi Liesi maytoline (Pyresmethrin), terallethrin;
(4) growth regulatory substance:
(a) chitin synthesis inhibitor: fluorine pyridine urea, diflubenzuron, flucycloxuron, flufenoxuron, HEXAFLUMURON, lufenuron, Rimon, Teflubenzuron, triflumuron, bistrifluron, noviflumuron, Buprofezin, hexythiazox, second mite azoles, clofentezine, pyrrole worm are swelled, penfluron;
(b) moulting hormone antagonist: chlorine worm hydrazides, methoxyfenozide, worm hydrazides, ring worm hydrazides, nimbin;
(c) neotonin sample material: pyriproxyfen, methoprene, difenolan, guarantor children ether, hydroprene, kinoprene, triprene;
(d) lipid biosynthesis inhibitor: spiral shell mite ester, Spiromesifen, spiral shell worm ethyl ester, flonicamid;
(5) nicotine receptor agonist/antagonist compound: the pyridine worm is clear, clothianidin, MTI-446, Provado, Ti304, thiacloprid, Diacloden, Diacloden, Nicotine, bensultap, cartap;
(6) GABA agonist compounds:
(a) clear, the methylene ethiprole of acetyl worm nitrile, ethiprole, fluorine worm, ethiprole, pyridine ethiprole;
(b) organochlorine system; Toxaphene, Niran, 5a,6,9,9a-hexahydro-6,9-methano-2,4, HCH, γ-HCH, heptachlor, methoxy-DDT
(7) large annular lactone sterilant: Avrmectin, emaricin, milbemectin, thunder cuticulin, pleocidin, ivermectin, plug draw rhzomorph, doractin, eprinomectin, moxidectin,
(8) METI I compound: fenazaquin, pyridaben, tebufenpyrad, Tolfenpyrad, phonetic worm amine, the pine of liking to be beautiful, fenpyroximate, ether mite ether, kelthane;
(9) METI II and III compound: acequinocyl, Fluacrypyrim, tubatoxin;
(10) take off the conjugant compound: bromothalonil, Niagara 9044, dinobuton, dinocap, DNOC;
(11) the phosphorylation inhibitor compound of oxidation: cyhexatin, diafenthiuron, fenbutatin oxide, propargite, azocyclotin;
(12) confuse the random compound of decortication: Tianjin falls to going out;
(13) mixed-function oxidase inhibitor compound: Piperonyl Butoxide;
(14) sodium channel blockers compound: indoxacarb, metaflumizone;
(15) microbial pesticide: BT agent, Insect Pathogenic viral agent, rileyi agent, the former thread microbial inoculum of oxyuriasis; Bacillus, white muscardine bacterium, black muscardine bacterium, paecilomyces, thuringiensin, Verticillium;
(16) the spider toxoreceptor is done medication: romidepsin, ring-type romidepsin, 24 yuan of ring-type romidepsins, comply with De Sai;
(17) octopamine is done medication: amitraz;
(18) blue Buddhist nun's alkali derivant is done medication: Flubendiamide, Rynaxypyr, cyanogen insect amide
(19) magnesium pungency atpase inhibitor: thiocyclam, disosultap (thiosultap), nereistoxin;
(20) food rcstriction agent: pymetrozine;
(21) mite growth inhibitor: clofentezine, second mite azoles;
(22) other material: different thiophene worm azoles, Bifenazate, pyridalyl, sulphur, azoles mite cyanogen, cyflumetofen, sulfanilamide (SN) mite ester, tetradifon, Chlorphenamidine, 1,3-dichloropropylene, DCIP, bromopropylate, benzoximate, the methaldehyde, ethyl pleocidin, fluorine worm pyrrole quinoline, benzoximate, bromopropylate, chinomethionate, G-23922, trichloronitromethane, Crewe Qi Yazuobian (Clothiazoben), CGA 183893, it spreads cruel auspicious nurse (Fenoxacrim) Fano, virtue fluorine amine (Fentrifanil), fluorine mite thiophene, fluorine mite piperazine, pink bollworm property lures element, Japanese beetle's sex attractant (Japonilure);
Figure GDA00003484046400441
Worm ketone, oil, potassium oleate, sulfluramid, Diphenylsulfide, triarathene;
Sterilant:
(1) benzoglyoxaline system: F-1991, derosal, fuberidazole, thiabendazole, thiophanate_methyl etc.;
(2) dicarboxyl imide series: chlozolinate, RP-26019, procymidone, Vinclozoline etc.;
(3) DMI-sterilant system: imazalil,
Figure GDA00003484046400442
Imidazoles, pefurazoate, prochloraz, fluorine bacterium azoles, triforine, pyrifenox, fenarimol, nuarimol, penta ring azoles, Bitertanol, bromuconazole, cyproconazole, difenoconazole, alkene azoles alcohol, epoxiconazole, RH-7592, fluquinconazole, fluzilazol, flutriafol, own azoles alcohol, imibenconazole, plant the bacterium azoles, metconazole, nitrile bacterium azoles, Topaze, Wocosin 50TK, prothioconazoles, simeconazoles, tebuconazole, fluorine ether azoles, triazolone, triadimenol, triticonazole, etaconazole, furconazole_cis-cis etc.;
(4) phenyl amide system: M 9834, furalaxyl, metaxanin, Metalaxyl-M,
Figure GDA00003484046400443
Frost spirit, ofurace etc.;
(5) amine system: ten dimorpholines, dodemorph, fenpropimorph, tridemorph, fenpropidin, pipron, volution bacterium amine etc.;
(6) thiophosphatephosphorothioate system: EDDP, iprobenfos, pyrazophos etc.;
(7) dithiode methane series: isoprothiolane etc.;
(8) carboxylic acid amides: benodanil, boscalid amine, carboxin, phenol Forlan (Off ェ Application Off ラ Application), fultolanil, good fortune Lapie, mebenil, oxycarboxin, pyrrole metsulfovax, thifluzamide etc.;
(9) hydroxyl-(2-is amino) pyrimidine system: bupirimate, dimethirimol, the phonetic phenol of second etc.;
(10) AP sterilant (anilino-pyrimidine) is: cyprodinil, mepanipyrim, phonetic mould amine etc.;
(11) N-phenylcarbamate system: the mould prestige of second etc.;
(12) QoI-sterilant (Qo inhibitor) is: Azoxystrobin, ZEN 90160, pyraclostrobin, kresoxim-methyl, oxime bacterium ester, dimoxystrobin, SSF 126, orysastrobin,
Figure GDA00003484046400451
Cycloheximide triazole, fluoxastrobin, fenamidone, SSF 126 etc.;
(13) PP sterilant (phenylpyrrole) is: fenpiclonil, fludioxonil etc.;
(14) quinoline system: quinoxyfen etc.;
(15) AH sterilant (aromatic hydrocarbon) is: biphenyl, chloroneb, dicloran, quintozene, tecnazene, tolclofosmethyl (ト Le Network ト Off ォ ス-メ チ Le) etc.;
(16) MBI-R system: phthalide, pyroquilon, tricyclazole etc.;
(17) MBI-D system: ring propionyl bacterium amine, two chlorine zarilamid, zarilamid etc.;
(18) SBI agent: fenhexamid, pyributicarb, Terbinafine etc.;
(19) phenylurea: pencycuron etc.;
(20) QiI-sterilant (Qi inhibitor): cyazofamid etc.;
(21) benzamide system: zoxamide etc.;
(22) enol pyranose aldehydic acid system: blasticidin, midolthromycin etc.;
(23) own pyranose base system: kasugamycin etc.;
(24) Glucopyranose base system: Streptomycin sulphate, jingganmycin etc.;
(25) malonamide nitrile system: white urea cyanogen etc.;
(26) carbamate system: iodine proyl n-butyl carbamate (iodocarb), Propamocarb, prothiocarb, polycarbamate etc.;
(27) take off conjugant: Niagara 9044, Mildex, ferimzone, fluazinam etc.;
(28) organo-tin compound: fentin acetate, fentin chloride, fentin hydroxide etc.;
(29) phosphoric acid ester: phosphorous acid, tolclofosmethyl, triethylphosphine acid etc.;
(30) phthalamidic acid system: tecloftalam etc.;
(31) phentriazine system: triazoxide etc.;
(32) benzsulfamide system: flusulfamide etc.;
(33) pyridazinone: diclomezine etc.;
(34) CAA sterilant (carboxylic acid amide) is: dimethomorph, flumorph, benzene metsulfovax, zinc 1,2-propylene bisdithiocarbamate, mandipropamid etc.;
(35) tsiklomitsin: terramycin etc.;
(36) thiocarbamate system: methasulfocarb etc.;
(37) other compound: etridiazole, polyoxin,
Figure GDA00003484046400461
Quinoline is sour, hydroxyl is different
Figure GDA00003484046400462
Azoles, octhilinone (オ Network チ ノ リ Application), Silthiopham, the difluoro woods, my acid benzene-S-methyl, probenazole, tiadinil, Guardian, cyflufenamid, the third oxygen quinoline, metrafenone, fluopicolide, copper hydroxide, organic copper, sulphur, Karbam Black, zinc manganese ethylenebisdithiocarbamate, maneb, Carbatene, zinc 1,2-propylene bisdithiocarbamate, thiuram, zineb, ziram, Vancide 89, Difolatan, Phaltan, m-tetrachlorophthalodinitrile, dichlofluanid, tolylfluanid, dodine, Guanoctine, iminoctadine triacetate, the iminoctadine dodecylbenzene sulfonate, anilazine, the Delan, trichloronitromethane, dazomet, metamsodium, chinomethionate, cyprofuram, Silthiopham, Agrobacterium, azoles furan grass etc.;
Plant-growth regulator:
Dormin, indolebutyric acid, uniconazole, indazole ester, ethrel, cloxyfonac, choline dichloride, chlorella extraction liquid, calcium peroxide, cyanamide, 2,4-drip propionic acid, Plant hormones regulators,gibberellins, daminozide, decyl alcohol, anti-fall ester, methyl piperidine, paclobutrazol, paraffin, Piperonyl Butoxide, pyrrole grass ether, flurprimidol, jasmonic propyl ester, Prohexadione calcium salt, benzylaminopurine, pendimethalin, forchlorfenuron, Regulox potassium, 1-naphthalene acetamide, 4-CPA, MCPB, choline, oxyquinoline sulfate, indazole ester, Ding Leling, 1-methylcyclopropene, RU-2267 hydrochloride;
Embodiment
Then, embodiment is shown, is described more specifically the present invention.But the present invention is not subjected to any restriction of following examples.
Embodiment 1
(i) 1-(3-bromo-5-chlorophenoxy)-and 3-(2-phenyl-propane-2-yl) manufacturing of urea
Figure GDA00003484046400471
3-bromo-5-chlorophenoxy phenyl carbamate (3.00g) is dissolved in the tetrahydrofuran (THF) (50ml).Add therein cumyl amine (1.54g) and triethylamine (1.15g), reflux stirred in lower 5 hours.Thereafter, reaction solvent is removed in underpressure distillation.The residue that obtains is passed through silica gel column chromatography (developing solvent; Hexane: ethyl acetate=3:1) is carried out thick purifying.With the coarse crystallization that the hexane washing obtains, obtain 1-(3-bromo-5-chlorophenoxy)-3-(2-phenyl-propane-2-yl) urea (2.89g, yield 86%).
1-(3-bromo-5-chlorophenoxy)-and 3-(2-phenyl-propane-2-yl) physical property of urea is as follows.
1H-NMR(CDCl 3/TMS,δ(ppm))7.39～7.17(m，9H),5.79(s，1H)，1.73(s，6H)
(ⅱ) 1-(3-bromo-5-chlorophenoxy)-and 1-ethyl-3-(2-phenyl-propane-2-yl) manufacturing of urea (compound number 1-24)
Figure GDA00003484046400472
With 1-(3-bromo-5-chlorophenoxy)-3-(2-phenyl-propane-2-yl) urea (2.89g) is dissolved in DMF (30ml).Add therein salt of wormwood (5.18g) and iodoethane (1.17g), stir an evening under the room temperature.Add ethyl acetate thereafter.With the aqueous ammonium chloride solution washing, make organic layer dry with sal epsom.After the filtration, the underpressure distillation desolventizing.The residue that obtains is passed through silica gel column chromatography (developing solvent; Hexane: ethyl acetate=5:1) carry out purifying obtains target 1-(3-bromo-5-chlorophenoxy)-1-ethyl-3-(2-phenyl-propane-2-yl) urea (2.86g, yield 92%).
1-(3-bromo-5-chlorophenoxy)-and 1-ethyl-3-(2-phenyl-propane-2-yl) physical property of urea is as follows.
1H-NMR(CDCl 3/TMS，δ(ppm))7.34～7.32（m,4H),7.28～7.22(m，3H)，7.15(t，1H)，5.91(s，1H)，3.60(qZH)，1.68(s,6H)，1.12(t，3H)
The example of the aryloxy carbamide compound of the present invention that can be made by preceding method etc. is shown in table 1～4.Substituting group in the compound of table 1 expression (a) expression.Substituting group in the compound of table 2 expression (b) expression.Substituting group in the compound of table 3 expression (c) expression.Substituting group in the compound of table 4 expression (d) expression.Should illustrate, table 1～4 only show the part of the aryloxy carbamide compound of the present invention that can be made by aforesaid method etc.According to the record of this specification sheets can easily understand for those skilled in the art other compound of not specifically illustrating in this manual, the compound that is replaced by various groups that namely do not break away from the spirit and scope of the invention can and can use by manufacturings such as aforesaid methods.
[table 1]
The 1st table
Figure GDA00003484046400491
[table 2]
The 1st table (continuing)
Figure GDA00003484046400501
[table 3]
The 1st table (continuing)
Figure GDA00003484046400511
[table 4]
The 1st table (continuing)
Figure GDA00003484046400521
[table 5]
L shows (continuing)
Figure GDA00003484046400531
[table 6]
The 1st table (continuing)
Figure GDA00003484046400541
[table 7]
The 1st table (continuing)
Figure GDA00003484046400551
[table 8]
The 1st table (continuing)
Figure GDA00003484046400561
[table 9]
The 1st table (continuing)
Figure GDA00003484046400571
[table 10]
The 1st table (continuing)
Figure GDA00003484046400581
Figure GDA00003484046400582
[table 11]
The 2nd table
Figure GDA00003484046400591
[table 12]
The 2nd table (continuing)
[table 13]
The 2nd table (continuing)
Figure GDA00003484046400611
[table 14]
The 2nd table (continuing)
Figure GDA00003484046400621
Figure GDA00003484046400622
[table 15]
The 3rd table
Figure GDA00003484046400631
Figure GDA00003484046400632
[table 16]
The 4th table
[table 17]
The 4th table (continuing)
Figure GDA00003484046400651
For the compound that belongs to the oil of thickness among the compound shown in table 1～3 (toughening oil (Visc.Oil) or vis) or belong to unbodied compound (amorphous (Amorphous) or amo) measures 1H-NMR(CDCl 3).Be shown in its measurement result following.
[table 18]
Figure GDA00003484046400661
[table 19]
Figure GDA00003484046400671
[table 20]
Figure GDA00003484046400681
[table 21]
Figure GDA00003484046400691
[table 22]
Figure GDA00003484046400701
[table 23]
[table 24]
Figure GDA00003484046400721
[table 25]
In addition, the example with the manufacturing intermediate of aryloxy carbamide compound of the present invention is shown in table 5～9.The example of the manufacturing intermediate of table 5 expression (e) expression.The example of the manufacturing intermediate of table 6 expression (f) expression.The example of the manufacturing intermediate of table 7 expression (d) expression.The example of the manufacturing intermediate of table 8 expression (g) expression.
[table 26]
The 5th table
Figure GDA00003484046400741
[table 27]
The 5th table (continuing)
Figure GDA00003484046400751
[table 28]
The 5th table (continuing)
Figure GDA00003484046400761
[table 29]
The 5th table (continuing)
Figure GDA00003484046400771
[table 30]
The 5th table (continuing)
Figure GDA00003484046400781
[table 31]
The 5th table (continuing)
Figure GDA00003484046400791
[table 32]
The 5th table (continuing)
Figure GDA00003484046400801
[table 33]
The 5th table (continuing)
[table 34]
The 5th table (continuing)
[table 35]
The 6th table
[table 36]
The 6th table (continuing)
Figure GDA00003484046400841
[table 37]
The 6th table (continuing)
Figure GDA00003484046400852
[table 38]
The 7th table
Figure GDA00003484046400861
Figure GDA00003484046400862
[table 39]
The 8th table
[table 40]
The 9th table
Figure GDA00003484046400881
Compound determination for the following compound number in the compound shown in table 5～9 1H-NMR(CDCl 3).Be shown in its measurement result following.
[table 41]
Figure GDA00003484046400891
The example of formulations of some noxious organism control agents of the present invention is shown, but additive and adding proportion should not be defined in these embodiment, can change at wide region.Part expression weight part in the example of formulations.Be shown in the example of formulations of agricultural or horticultural use following.
Example of formulations 1(wettable powder)
With the fine pulverizing of above even mixing, obtain the wettable powder of effective constituent 40%.
Example of formulations 2(emulsion)
With above mixed dissolution, obtain the emulsion of effective constituent 30%.
The example of formulations that epidemic prevention is used with animal is shown in following.
Example of formulations 3(particle)
5 parts of the compounds of this invention
94 parts of kaolin
1 part of white carbon black
The compounds of this invention is dissolved in the organic solvent, after the carrier spraying, makes the lower evaporation of solvent decompression.This particle can mix with the animal bait.
Example of formulations 4(injection)
0.1～1 part of the compounds of this invention
The peanut oil balance
Pass through the sterilising filter filtration sterilization after the preparation.
Example of formulations 5(sprinkling agent)
5 parts of the compounds of this invention
10 parts of myristinates
The Virahol balance
Example of formulations 6(drops)
10～15 parts of the compounds of this invention
10 parts of cetylates
The Virahol balance
Example of formulations 7(sprays)
1 part of the compounds of this invention
10 parts of propylene glycol
The Virahol balance
(biological test)
Demonstrating the compounds of this invention by following test example is useful as acaricidal effective constituent.
The potency test of 1 pair of T.urticae Koch of test example (Tetranychus urticae)
After germinateing, the French beans of sowing through on first leaf of 7～10 days, inoculate the T.urticae Koch female adult worm of 10 organic phosphate agent resistances in 3 cun basins.Then, the emulsion for preparing prescription shown in the above-mentioned example of formulations 2.This emulsion is diluted with water to compound concentration reaches 125ppm, this diluent is interspersed among above-mentioned French beans.These French beans are placed in the thermostatic chamber of 25 ℃ of temperature, humidity 65%.From the life and death of dissemination through 3 days " Invest, Then Investigate " adults.The ovum of giving birth to through 14 days " Invest, Then Investigate "s from dissemination could develop into adult.
To containing respectively compound number 1-3,1-10,1-20,1-21,1-24,1-25,1-26,1-27,1-28,1-29,1-30,1-39,1-41,1-42,1-50,1-51,1-54,1-55,1-56,1-57,1-60,1-61,1-62,1-63,1-65,1-66,1-67,1-68,1-71,1-94,1-96,1-97,1-98,1-99,1-101,1-102,1-103,1-108,1-109,1-110,1-111,1-114,1-116,1-118,1-119,1-120,1-121,1-122,1-124,1-125,1-126,1-129,1-130,1-132,1-133,1-134,1-135,1-136,1-137,1-138,1-140,1-149,1-152,1-160,1-161,1-171,1-177,1-178,1-179,1-180,1-181,1-182,1-183,1-184,1-185,1-186,1-187,1-188,1-189,1-190,1-191,1-192,1-193,1-194,1-196,1-197,1-198,1-199,1-200,1-201,1-202,1-203,1-204,1-205,1-206,1-207,1-209,1-211,1-212,1-213,1-214,1-215,1-216,1-217,1-218,1-220,1-221,1-222,1-223,1-224,1-226,1-227,1-228,1-229,1-230,1-232,1-233,1-234,1-235,1-236,1-237,2-1,2-2,2-4,2-6,2-7,2-8,2-10,2-11,2-13,2-24,2-26,2-33,2-37,2-39,2-40,2-42,2-44,2-46,2-47,2-50,2-51,2-52,2-53,2-55,2-56,2-57,2-58,2-59,2-60,2-61,2-62,2-63,2-64,2-65,2-66,2-67,2-68,2-71,2-72,3-3, and the emulsion of the compound of 3-22 carries out above-mentioned test.Killing rate when its result, any compound are diluted to concentration and are 125ppm is more than 90%.
The potency test of 2 pairs of citrus red mite (crm)s of test example (Panonychus citri)
The citrus red mite (crm) female adult worm that produces in 8 Prefectura de Kanagawa of orange leaf inoculation of putting into culture dish.Then, the emulsion for preparing prescription shown in the above-mentioned example of formulations 2.The concentration that this emulsion is diluted with water to compound reaches 125ppm, this diluent is scattered tower with rotation be dispersed on the above-mentioned orange.This orange is placed in the thermostatic chamber of 25 ℃ of temperature, humidity 65%.From the life and death of dissemination through 3 days " Invest, Then Investigate " adults.The ovum of giving birth to through 10 days " Invest, Then Investigate "s from dissemination could develop into adult.
To containing respectively compound number 1-3,1-8,1-10,1-24,1-50,1-110,1-111,1-114,1-116,1-119,1-120,1-121,1-122,1-123,1-124,1-129,1-134,1-135,1-149,1-152,1-161,1-171,1-177,1-178,1-179,1-180,1-181,1-182,1-183,1-184,1-185,1-186,1-187,1-188,1-189,1-190,1-192,1-193,1-194,1-197,1-199,1-200,1-201,1-202,1-204,1-205,1-206,1-207,1-209,1-211,1-212,1-213,1-214,1-215,1-216,1-218,1-220,1-222,1-224,1-227,1-229,1-230,1-233,1-234,1-235,1-236,1-237,2-1,2-2,2-4,2-6,2-7,2-10,2-11,2-21,2-33,2-37,2-39,2-40,2-44,2-50,2-51,2-52,2-53,2-55,2-56,2-57,2-59,2-60,2-61,2-62,2-63,2-64,2-65,2-66,2-67,2-68, and the emulsion of the compound of 2-71, carry out above-mentioned test.Killing rate when its result, any compound are diluted to concentration and are 125ppm is more than 90%.
The potency test of 3 pairs of citrus red mite (crm)s of test example (Panonychus citri)
Inoculate the citrus red mite (crm) female adult worm of the miticide resistance of 8 Wakayama Ken's products at the orange leaf of putting into culture dish.Then, the emulsion for preparing prescription shown in the above-mentioned example of formulations 2.The concentration that this emulsion is diluted with water to compound reaches 125ppm, this diluent is scattered tower with rotation be dispersed on the above-mentioned orange.This orange is placed in the thermostatic chamber of 25 ℃ of temperature, humidity 65%.From the life and death of dissemination through 3 days " Invest, Then Investigate " adults.The ovum of giving birth to through 10 days " Invest, Then Investigate "s from dissemination could develop into adult.
Emulsion to the compound that contains respectively compound number compound number 1-20,1-26,1-27,1-28,1-29,1-35,1-41,1-42,1-51,1-60,1-61,1-63,1-65,1-66,1-67,1-68,1-98,1-99,1-101,1-116,1-124,1-161,1-186,1-189,1-230,2-8,2-13,2-26 and 2-50 carries out above-mentioned test.Killing rate when its result, any compound are diluted to concentration and are 125ppm is more than 90%.
The potency test of 4 pairs of kamisawa tetranychus of test example (Tetranychus kanzawai)
After germinateing, the French beans of sowing through on first leaf of 7～10 days, inoculate the kamisawa tetranychus female adult worm that produce 10 Okayama County in 3 cun basins.Then, the emulsion for preparing prescription shown in the above-mentioned example of formulations 2.This emulsion is diluted with water to compound concentration reaches 500ppm or 125ppm, this diluent is interspersed among above-mentioned French beans.These French beans are placed in the thermostatic chamber of 25 ℃ of temperature, humidity 65%.From the life and death of dissemination through 3 days " Invest, Then Investigate " adults.The ovum of giving birth to through 14 days " Invest, Then Investigate "s from dissemination could develop into adult.
To containing respectively compound number 1-8,1-10,1-11,1-13,1-16,1-19,1-20,1-21,1-24,1-26,1-27,1-28,1-29,1-30,1-41,1-42,1-43,1-46,1-47,1-48,1-56,1-57,1-58,1-60,1-61,1-62,1-63,1-67,1-66,1-71,1-74,1-80,1-94,1-95,1-96,1-98,1-100,1-102,1-104,1-106,1-108,1-109,1-110,1-111,1-115,1-118,1-119,1-121,1-122,1-123,1-124,1-125,1-126,1-127,1-131,1-140,1-144,1-209,1-212,1-218,1-220,1-224,1-225,1-232,1-234,1-235,1-236,2-12,2-22,2-23,2-24,2-34,2-41,2-47,2-55,2-56,3-2,3-3,3-4, and the emulsion of the compound of 4-5, carry out above-mentioned test.Killing rate when its result, any compound are diluted to concentration and are 500ppm is more than 90%.
To containing respectively compound number 1-3,1-25,1-39,1-40,1-50,1-51,1-53,1-55,1-64,1-65,1-66,1-68,1-93,1-97,1-99,1-101,1-103,1-114,1-116,1-120,1-129,1-130,1-132,1-135,1-136,1-137,1-149,1-150,1-152,1-161,1-162,1-171,1-177,1-178,1-179,1-181,1-182,1-183,1-184,1-185,1-186,1-187,1-188,1-189,1-190,1-191,1-192,1-193,1-194,1-196,1-197,1-198,1-199,1-200,1-201,1-202,1-203,1-204,1-205,1-206,1-207,1-211,1-213,1-214,1-215,1-216,1-222,1-223,1-226,1-227,1-228,1-229,1-230,1-233,1-237,2-5,2-6,2-8,2-10,2-13,2-21,2-26,2-33,2-37,2-39,2-40,2-42,2-44,2-46,2-50,2-51,2-52,2-53,2-57,2-58,2-59,2-60,2-61,2-62,2-63,2-64,2-65,2-66,2-67,2-68,2-71,2-72, the emulsion of the compound of 2-76 and 3-22 carries out above-mentioned test.Killing rate when its result, any compound are diluted to concentration and are 125ppm is more than 90%.
The potency test of 5 pairs of tangerine peroniums of test example goitre mite (Aculops pelekassi)
Putting into 20 miticide resistance tangerine peronium goitre mite adults of orange leaf inoculation of culture dish.Then, the emulsion for preparing prescription shown in the above-mentioned example of formulations 2.The concentration that this emulsion is diluted with water to compound reaches 125ppm, this diluent is scattered tower with rotation be dispersed on the above-mentioned orange.This orange is placed in the thermostatic chamber of 25 ℃ of temperature, humidity 65%.From the life and death of dissemination through 3 days " Invest, Then Investigate " adults.The ovum of giving birth to through 10 days " Invest, Then Investigate "s from dissemination could develop into adult.
Emulsion to the compound that contains respectively compound number 1-3,1-8,1-9,1-10,1-13,1-24,1-25,1-26,1-27,1-28,1-29,1-30,1-41,1-42,1-50,1-51,1-55,2-1,2-2,2-4,2-6,2-7,2-8,2-9,2-10,2-11,2-13,2-21,2-24 and 2-33 carries out above-mentioned test.Killing rate when its result, any compound are diluted to concentration and are 125ppm is more than 90%.
The insecticidal test of 6 pairs of haemaphysalis longicornises of test example (Haemaphysalis longicornis)
Adding the compounds of this invention concentration in the vial of 20mL volume is the acetone soln 0.118ml of 400ppm.The limit makes the vial rotation, and the limit to the vial inner blower, makes the acetone volatilization with blower, makes film at the bottle inwall.The inner wall surface area of the vial that uses is 47cm 2, therefore processing dose is 1 μ g/cm 2
Put the young mite of 15～40 haemaphysalis longicornises in this bottle, close the cover is accommodated in thermostatic chamber (25 ℃, black dull lower).
Through after 1 day and through 2 days dead borer populations of " Invest, Then Investigate ", calculate dead worm rate by following calculating formula.
Dead worm rate (%)=(dead true tick number)/(for the true tick number of test) * 100
Compound for compound number 1-161,2-1,2-13 and 2-26 carries out above-mentioned test.Its result, the dead worm rate of any compound is 100%.
By above result as can be known, the compounds of this invention demonstrates excellent killing action to mite.
Utilize possibility on the industry
Aryloxy carbamide compound of the present invention or its salt can be prevented and kill off the harmful organism that becomes problem aspect farm crop, the health.Can effectively prevent and kill off mite class and/or pathogenic mushroom especially.

Claims (5)

1. aryloxy carbamide compound or its salt of formula (I) expression;
Figure FDA00003026539200011
In the described formula (I), Cy represents C6～10 aryl or heteroaryl;
X represents without replacement or substituent C1～6 alkyl is arranged, without replacing or substituent C3～8 cycloalkyl being arranged, without replacing or substituent C2～6 alkenyls being arranged, without replacing or substituent C2～6 alkynyls being arranged, hydroxyl, without replacing or substituent C1～6 alkoxyl groups being arranged, amino, without replacing or substituent C1～6 alkylaminos being arranged, without replacing or substituent C1～7 acyl groups being arranged, without replacing or substituent C1～6 alkoxy carbonyls being arranged, without replacing or substituent C1～6 alkyl sulphonyls being arranged, without replacing or substituent C1～6 alkoxyl group alkylsulfonyls being arranged, without replacing or substituent C6～10 aryl being arranged, without replacing or substituent heteroaryl being arranged, without replacing or substituent oxyimino C1～6 alkyl being arranged, nitro, cyano group, perhaps halogen atom;
N represents the number of the X on the Cy and is arbitrary integer in 0～5; N is 2 when above, and X can be mutually the same, also can differ from one another; In addition, n is 2 when above, and X can be together together forms ring with carbon atom or the nitrogen-atoms of bonding;
R 1Expression without replace or have substituent C1～6 alkyl, without replace or have substituent C2～6 alkenyls, without replace or substituent C2～6 alkynyls are arranged, without replacing or substituent C1～7 acyl groups being arranged or without replacing or substituent C1～6 alkoxy carbonyls being arranged;
Q represents the group that formula II, formula III or formula IV represent;
In the described formula II, * represents bonding position; R 2The expression hydrogen atom, without replace or have substituent C1～6 alkyl, without replace or have substituent C2～6 alkenyls, without replace or substituent C2～6 alkynyls are arranged, without replacing or substituent C1～7 acyl groups being arranged or without replacing or substituent C1～6 alkoxy carbonyls, R being arranged 1With R 2Can form together the nothing replacement or substituent C2～4 alkylidene groups are arranged;
R 3And R 4Represent independently of one another hydrogen atom, without replace or have substituent C1～6 alkyl, without replace or have substituent C2～6 alkenyls, without replace or have substituent C2～6 alkynyls, without replace or substituent C6～10 aryl are arranged, without replacing or substituent heteroaryl or cyano group being arranged; At this, R 3With R 4Can be together together form ring with the carbon atom of bonding;
R 5Expression is without replacement or substituent C1～6 alkyl are arranged, without replacing or substituent C3～8 cycloalkyl being arranged, without replacing or substituent C2～6 alkenyls being arranged, without replacing or substituent C2～6 alkynyls being arranged, without replacing or substituent C1～7 acyl groups being arranged, carboxyl, without replacing or substituent C1～6 alkoxy carbonyls being arranged, without replacing or substituent C2～6 alkenyl oxy carbonyls being arranged, without replacing or substituent C2～6 alkynyloxy base carbonyls being arranged, without replacing or substituent aminocarbonyl being arranged, without replacing or substituent C6～10 aryl being arranged, without replacing or substituent heteroaryl being arranged, without replacing or substituent oxyimino C1～6 alkyl being arranged, perhaps cyano group;
Figure FDA00003026539200021
In the described formula III, * represents bonding position; R 6And R 7Independently of one another expression without replace or have substituent C1～6 alkyl, without replace or have substituent C3～8 cycloalkyl, without replace or have substituent C2～6 alkenyls, without replace or substituent C2～6 alkynyls are arranged, without replacing or substituent C6～10 aryl being arranged or without replacing or substituent heteroaryl being arranged; At this, R 6With R 7Can be together together form ring with the sulphur atom of bonding;
In the described formula IV, * represents bonding position; R 2With above-mentioned expression equivalent; R 8Expression without replace or have substituent C3～8 cycloalkyl, without replace or substituent C1～6 alkoxy carbonyls are arranged, without replacing or substituent C6～10 aryl being arranged or without replacing or substituent heteroaryl being arranged;
Z represents Sauerstoffatom or sulphur atom.
2. the aryloxy carbamide compound of formula (I) expression is aryloxy carbamide compound or its salt that formula V represents,
Figure FDA00003026539200023
In the described formula V, R 1～R 5, X, n and Z and above-mentioned expression equivalent.
3. noxious organism control agent wherein, contains be selected from claim 1 or 2 described aryloxy carbamide compounds or its salt at least a kind as effective constituent.
4. miticide wherein, contains be selected from claim 1 or 2 described aryloxy carbamide compounds or its salt at least a kind as effective constituent.
5. sterilant wherein, contains be selected from claim 1 or 2 described aryloxy carbamide compounds or its salt at least a kind as effective constituent.
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